(Z)-(1R,8R)-10,10-dimethyl-9,11-dioxabicyclo[6.3.0]undec-4-ene | 37940-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-(1R,8R)-10,10-dimethyl-9,11-dioxabicyclo[6.3.0]undec-4-ene
• 英文别名: (1R,8R)-10,10-dimethyl-9,11-dioxabicyclo[6.3.0]undec-4-ene；5-Cycloocten-trans-1,2-diol-isopropyliden-ketal；(3aR,6Z,9aR)-2,2-dimethyl-3a,4,5,8,9,9a-hexahydrocycloocta[d][1,3]dioxole
• CAS: 37940-17-3
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: IFSHAVQLEMPLRA-HWKXXFMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-(1R,8R)-10,10-dimethyl-9,11-dioxabicyclo[6.3.0]undec-4-ene 在 盐酸 、 溴 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 7.0h， 生成 (1R,2R,5R,6S)-5-bromo-9-oxabicyclo[4.2.1]-nonan-2-ol
  参考文献：
  名称：

  Synthesis of Optically Active 9-Oxabicyclo[3.3.1]nona-2,6-diene as a Cycloocta-1,5-diene Equivalent and the Corresponding Tetrol

  摘要：

  Highly enantio- and diastereo-selective synthesis of C-2-symmetric 9-oxabicyclo[3.3.1]nona-2,6-diene and the corresponding C-2-symmetric 2,3,6,7-tetrol has been achieved starting from optically active 5-cyclooctene-1,2-diol prepared by an enzymatic procedure. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00089-2
• 作为产物：
  描述：

  (4R,5R)-4,5-dibut-3-enyl-2,2-dimethyl-1,3-dioxacyclopentane 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以89%的产率得到(Z)-(1R,8R)-10,10-dimethyl-9,11-dioxabicyclo[6.3.0]undec-4-ene
  参考文献：
  名称：

  An asymmetric synthesis of enantiopure chair and twist trans-cyclooctene isomers

  摘要：

  A pair of enantiopure chair and twist trans-cyclooctenes isomers were prepared by regioselective Sharpless asymmetric dihydroxylation of the central olefin of (E)-1,5,9-dectriene triene, with subsequent ring-closing metathesis to form an enantiomerically pure cis-cyclooctene. Epoxidation and ring-opening with lithium diphenylphosphide gives after oxidation two diastereomeric hydroxyphosphine oxides. Separate syn-elimination of these diastereomers gives enantiomerically pure chair and twist trans-cyclooctenes. A discussion of the molecular motion required to achieve the chair and twist isomers is discussed with reference to the X-ray crystal structure obtained for the hydroxyphosphine oxide leading to the chair trans-cyclooctene. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.036

文献信息

• Golding, Bernard T.; Sell, Charles S.; Sellars, Philip J., Journal of the Chemical Society. Perkin transactions II, 1980, p. 961 - 970
  作者：Golding, Bernard T.、Sell, Charles S.、Sellars, Philip J.

  DOI：——

  日期：——
• A Photochemical Synthesis of Functionalized <i>trans</i>-Cyclooctenes Driven by Metal Complexation
  作者：Maksim Royzen、Glenn P. A. Yap、Joseph M. Fox

  DOI：10.1021/ja8001919

  日期：2008.3.1

  Described is a scalable procedure for driving photochemical sytheses of trans-cyclooctene derivatives through metal complexation. During photoirradiation, reaction mixtures are continuously pumped through a column of a AgNO(3)-impregnated silica gel. The trans-cyclooctene derivative is selectively retained by the AgNO3-impregnated silica, but the cis-isomer elutes from the column back to the reaction flask, where it is photoisomerized and recirculated through the column. The method provides access to a range of usefully functionalized derivatives of trans-cyclooctene, including a derivative of 5-aza-trans-cyclooctene that underwent transannular cyclization upon treatment with bromine. The alkene stereochemistry is transferred with high fidelity to the hexahydropyrrolizine framework in the transannular cyclization.