136758-36-6

Usage

Explanation

The molecular formula represents the number of carbon (C), hydrogen (H), and oxygen (O) atoms in the compound, which is 9, 16, and 3 respectively.

Explanation

A spiroketal is an organic compound containing a spiro ring system, which is composed of a cyclic ether and an acetal.

Explanation

The compound has a spiro ring system consisting of two fused rings, one with six members and the other with five members, both containing oxygen atoms.

Explanation

The stereochemistry of the compound is defined by the configuration of the three chiral centers in the molecule, which are labeled as 4.alpha., 5.alpha., and 6.beta.

Explanation

Due to its unique structure and properties, 1,7-Dioxaspiro5.5undecane-4,5-diol, (4.alpha.,5.alpha.,6.beta.)has potential applications in the development of new drugs and chemical products.

Explanation

The compound has three chiral centers, which are carbon atoms with four different groups attached, leading to different spatial arrangements of the molecule.

Type of Compound

Spiroketal

Spiro Ring System

Six-membered oxygen-containing ring fused to a five-membered oxygen-containing ring

Stereochemistry

(4.alpha.,5.alpha.,6.beta.)

Potential Applications

Pharmaceutical and Chemical Industries

Chirality

Three chiral centers

Upstream product

• 113297-14-6 1,7-dioxaspiro<5.5>undec-4-ene 
• 189508-45-0 (5S,6S)-1,7-Dioxa-spiro[5.5]undec-3-en-5-ol 
• 191659-53-7 C₉H₁₄O₃ 

Relevant academic research and scientific papers

Synthesis of a new spiroacetal based herbicide

[3R*, 5S*, 6S*]-3-Benzyloxy-5-methoxy- 1,7-dioxaspiro[5.5]undecane 3 and [3R*, 5S*, 6S*]-3-methoxy-5-benzyloxy-1,7-dioxaspiro[5.5]undecane 4 were prepared making use of a base induced rearrangement of a 4,5-epoxy-1,7-dioxaspiro[5.5]undecane.

Crystal structures of (3S*,4S*,5S*,6S*)-3,4-epoxy-1,7-dioxaspiro[5.5]undecan- 5-ol, (3R*,5S*,6S*)-1,7-dioxaspiro[5.5]undecane-3,5-diyl diacetate and (4S*,5S*,6S*)-1,7-dioxaspiro[5.5]undecane-4,5-diol

The structures of (3S*,4S*,5S*,6S*)-3,4-epoxy-1,7-dioxaspiro[5.5]undecan- 5-ol (2), (3R*,5S*,6S*)-1,7-dioxaspiro[5.5]undecane-3,5-diyl diacetate (4) and (4S*,5S*,6S*)-1,7-dioxaspiro[5.5]undecane-4,5-diol (5) have been determined by X-ray crystallography. The unsubstituted tetrahydropyran ring in (2) adopts an axial position with respect to the epoxy-substituted ring and the hydroxy group at C 5 is syn to the epoxide group. Intermolecular hydrogen bonding is observed between the C 5 hydroxy group and O1. The two six-membered rings in (4) adopt chair conformations and the two acetate groups adopt 1,3-diaxial positions. The C 5 hydroxy group in (5) assumes an axial position anti to the C-O bond of the neighbouring ring whilst 4-OH occupies an equatorial position. Intermolecular hydrogen bonding is also observed between 4-OH and 5-OH. Compound (2), C9H14O4, M 186.21, crystallized in the monoclinic space group P21/c with a 7.867(1), b 12.2060(9), c 9.3676(8) A, β 102.744(8)°, V 877.4(1) A3 and No 1163 [I > 2.5σ(I)], R 0.031, Rw 0.035. Compound (4), C13H20O6, M 272.30, crystallized in the triclinic space group P1 with a 9.902(1), b 11.0024(9), c 6.9183(5) A, α 104.078(8), β 96.769(9), γ 101.980(8)°, V 703.8(1) A3, No 1657 [I > 2.5σ(I)], R 0.047, Rw 0.044. Compound (5), C9H16O4, M 188.22, crystallized in the orthorhombic space group Pbca with a 25.504(3), b 8.909(2), c 8.038(2) A, V 1826.4(5) A3, No 1096 [I > 2.5σ(I)], R 0.030, Rw 0.030.

Dihydroxylation of 1,7-Dioxaspiroundec-4-enes

The highly stereoselective syn-hydroxylation of the unsaturated spiro acetals (4-8) with osmium tetraoxide is reported.In all cases, hydroxylation occurred from the β-face giving the diols in which the hydroxy group at C5 is axial and anti to the C-O bond of the neighbouring tetrahydropyran ring.