prop-2-enyl-bis[(1S,2R,3S,5S)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]borane

Base Information

• Chemical Name: prop-2-enyl-bis[(1S,2R,3S,5S)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]borane
• CAS No.: 106356-53-0
• Molecular Formula: C23H39 B
• Molecular Weight: 326.374
• Hs Code.: 2931900090
• European Community (EC) Number: 628-167-0
• DSSTox Substance ID: DTXSID00450243
• Nikkaji Number: J1.529.082J
• Wikidata: Q76416344
• Mol file: 106356-53-0.mol

Synonyms:106356-53-0;(+)-Ipc2B(allyl), 1M in dioxane;prop-2-enyl-bis[(1S,2R,3S,5S)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]borane;DTXSID00450243;ZIXZBDJFGUIKJS-AXSQLCHVSA-N;AKOS025294027;J-001580;allylbis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane;Allylbis[(1beta,5beta)-2alpha,6,6-trimethylbicyclo[3.1.1]heptane-3beta-yl]borane

Chemical Property of prop-2-enyl-bis[(1S,2R,3S,5S)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]borane

Chemical Property:

• Boiling Point: 100-102 °C
• Flash Point: 12 °C
• PSA: 0.00000
• Density: 0.961 g/mL at 25 °C
• LogP: 6.81180
• Storage Temp.: ?20°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 326.3144814
• Heavy Atom Count: 24
• Complexity: 476

Purity/Quality:

98%,99%, ^*data from raw suppliers

(+)-Ipc2B(allyl)borane solution 1 M in pentane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn,N
• Hazard Codes: F,Xn,N
• Statements: 11-19-36/37-40-66-67-65-51/53-36/37/38
• Safety Statements: 26-36/37-62-61-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(CC=C)(C1CC2CC(C1C)C2(C)C)C3CC4CC(C3C)C4(C)C
• Isomeric SMILES: B(CC=C)([C@H]1C[C@H]2C[C@@H]([C@@H]1C)C2(C)C)[C@H]3C[C@H]4C[C@@H]([C@@H]3C)C4(C)C
• Uses: This allylboration reagent is a convenient, salt-free, stable solution of a chiral allyl borane for asymmetric allylation of aldehydes leading to chiral homoallylic alcohols.

Technology Process of prop-2-enyl-bis[(1S,2R,3S,5S)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]borane

There total 9 articles about prop-2-enyl-bis[(1S,2R,3S,5S)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]borane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

B-chlorodiisopinocampheylborane (112246-73-8) + allylmagnesium bromide (1730-25-2) → B-allyldiisopinocampheylborane (106356-53-0)

Guidance literature:

In diethyl ether; at 0 - 20 ℃; for 1h;

DOI:10.1016/S0040-4020(02)00819-0

Reference yield:

(-)-B-methoxydiisopinocamphenylborane + allylmagnesium bromide (1730-25-2) → (-)-B-allyldiisopinocampheylborane (85116-38-7,106356-53-0)

Guidance literature:

In diethyl ether; at -78 - 20 ℃; for 1.25h;

DOI:10.1021/ol0159569

Reference yield:

(+)-B-methoxydiisocamphenylborane (99438-28-5) + allylmagnesium bromide (1730-25-2) → B-allyldiisopinocampheylborane (106356-53-0)

Guidance literature:

In diethyl ether; at -78 - 20 ℃;

DOI:10.1021/ol027538p DOI:10.1021/ol0504650

upstream raw materials:

(+)-B-methoxydiisocamphenylborane

allylmagnesium bromide

B-chlorodiisopinocampheylborane

allylmagnesium bromide

Downstream raw materials:

(4R,5S)-5-Methyl-hept-1-en-4-ol

(4S,5S)-5-Methyl-hept-1-en-4-ol

(S)-1-(pyridin-3-yl)but-3-en-1-ol

(R)-1-(pyridin-3-yl)but-3-en-1-ol

Refernces

• 1、 Marco, J. Alberto,García-Pla, Jorge,Carda, Miguel,Murga, Juan,Falomir, Eva,Trigili, Chiara,Notararigo, Sara,Díaz, J. Fernando,Barasoain, Isabel. "Design and synthesis of pironetin analogues with simplified structure and study of their interactions with microtubules". . p. 1630 - 1637. Retrieved 2011.
• 2、 Smith III, Amos B.,Ott, Gregory R.. "Total syntheses of (-)-macrolactin a, (+)-macrolactin e, and (-)- macrolactinic acid: An exercise in stille cross-coupling chemistry". . p. 3935 - 3948. Retrieved 1998.
• 3、 Sasaki, Makoto,Iwasaki, Kotaro,Arai, Keisuke. "Studies toward the Total Synthesis of Caribbean Ciguatoxin C-CTX-1: Synthesis of the LMN-Ring Fragment through Reductive Olefin Cross-Coupling". . p. 7163 - 7166. Retrieved 2018.
• 4、 Pfeiffer, Bernhard,Speck-Gisler, Sandra,Barandun, Luzi,Senft, Ursula,De Groot, Claire,Lehmann, Irene,Ganci, Walter,Gertsch, Juerg,Altmann, Karl-Heinz. "Total synthesis and configurational assignment of the marine natural product haliclamide". . p. 2553 - 2563. Retrieved 2013/05/22.