((7R,8R)-8-Isopropenyl-1,4-dioxa-spiro[4.5]dec-7-yl)-methanol | 123966-84-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((7R,8R)-8-Isopropenyl-1,4-dioxa-spiro[4.5]dec-7-yl)-methanol
• 英文别名: [(7R,8R)-8-prop-1-en-2-yl-1,4-dioxaspiro[4.5]decan-7-yl]methanol
• CAS: 123966-84-7
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: NJOAQFRSZVSFIV-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((7R,8R)-8-Isopropenyl-1,4-dioxa-spiro[4.5]dec-7-yl)-methanol 在 戴斯-马丁氧化剂 作用下， 以99%的产率得到(7R,8R)-8-Isopropenyl-1,4-dioxa-spiro[4.5]decane-7-carbaldehyde
  参考文献：
  名称：

  Studies toward the total synthesis of YW3699, a sesterterpenoid GPI biosynthesis inhibitor: preparation of the tri-substituted cyclooctene ring using the RCM reaction

  摘要：

  The preparation of eight-membered carbocycles with tri-substituted double bonds has been attempted using RCM reactions. One of the stereoisomers subjected to the RCM reaction provided a desired compound which will be used for the synthesis of YW3699. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.163
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到((7R,8R)-8-Isopropenyl-1,4-dioxa-spiro[4.5]dec-7-yl)-methanol
  参考文献：
  名称：

  Studies toward the total synthesis of YW3699, a sesterterpenoid GPI biosynthesis inhibitor: preparation of the tri-substituted cyclooctene ring using the RCM reaction

  摘要：

  The preparation of eight-membered carbocycles with tri-substituted double bonds has been attempted using RCM reactions. One of the stereoisomers subjected to the RCM reaction provided a desired compound which will be used for the synthesis of YW3699. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.163

文献信息

• Stereoselective reactions. 15.1 total synthesis of (+)-ivalin by utilizing asymmetric double alkylation reaction of α,β-unsaturated aldimine
  作者：Kiyoshi Tomioka、Fumio Masumi、Toyoharu Yamashita、Kenji Koga

  DOI：10.1016/0040-4020(89)80093-6

  日期：1989.1

  synthesis of (+)-ivalin (4), a representative of antileukemic eudesmane sesquiterpenes, is described. The ene-aldehyde (6) was converted to the nearly optically pure alcohol (20) through the asymmetric double a1ky1ation reaction of the chiral ene-enamine (14). The ene-carbonyl cyclization of (25) with tin(IV) chloride afforded the core skeleton (26). The stereoinversion of hydroxyl group and further transformation

  描述了不对称全合成的（+）-艾维林（4），是抗泛素的杜仲倍半萜烯的代表。通过手性烯-烯胺（14）的不对称双烷基化反应，将烯醛（6）转化为几乎光学纯的醇（20）。用氯化锡（IV）对（25）进行烯-羰基环化，得到核心骨架（26）。羟基的立体转化和进一步的转化提供了（+）-艾维林（4）。