(1S,3S)-1,2,3-环庚烷三醇 | 607403-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1S,3S)-1,2,3-环庚烷三醇
• 英文名称: cycloheptane-1,2,3-triol
• 英文别名: (1S,3S)-Cycloheptane-1,2,3-triol
• CAS: 607403-65-6
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: TWRHYWIUMGRADE-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯甲醛二甲缩醛 、 (1S,3S)-1,2,3-环庚烷三醇 在 camphor-10-sulfonic acid 作用下， 以 乙腈 为溶剂， 以56%的产率得到(1S,2R,3S)-2,3-O-benzylidene cycloheptanol
  参考文献：
  名称：

  Highly stereoselective synthesis of a seven-membered carbasugar via triisobutylaluminium promoted Claisen rearrangement

  摘要：

  2-Methylene-5-vinyl-tetrahydrofuran derivative 6 was obtained from alpha-D-glucose. Treatment of 6 with triisobutylaluminium (TIBAL) induced Claisen expansion reaction to give the seven-membered carbasugar derivative 7, which represents a new type of chiral building blocks. The rearrangement reaction has been proved to be highly stereoselective. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00490-7
• 作为产物：
  描述：

  (3R,4S,5R)-3,4-Bis-benzyloxy-5-vinyl-dihydro-furan-2-one 在 palladium on activated charcoal 吡啶 、 氢气 、 三异丁基铝 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， -78.0~80.0 ℃ 、379.21 kPa 条件下， 生成 (1S,3S)-1,2,3-环庚烷三醇
  参考文献：
  名称：

  Highly stereoselective synthesis of a seven-membered carbasugar via triisobutylaluminium promoted Claisen rearrangement

  摘要：

  2-Methylene-5-vinyl-tetrahydrofuran derivative 6 was obtained from alpha-D-glucose. Treatment of 6 with triisobutylaluminium (TIBAL) induced Claisen expansion reaction to give the seven-membered carbasugar derivative 7, which represents a new type of chiral building blocks. The rearrangement reaction has been proved to be highly stereoselective. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00490-7

文献信息

• Conversion of racemic allylic hydroperoxides into corresponding chiral 1/2,3-triols by using catalytic OsO$_{4}$ and chiral cinchona ligands in the absence of co-oxidant
  作者：Haydar GÖKSU、Mehmet Serdar GÜLTEKİN

  DOI：10.3906/kim-1411-68

  日期：——

  For the first time, removal of oxygen atoms from allylic hydroperoxide functionality and reintroduction to the double bond was achieved using catalytic OsO$_4}$ and chiral cinchona alkaloid derivatives in an acetone-water mixture to give corresponding chiral 1/2,3-triol with an enantioselectivity up to 99% ee. The hydroperoxide group was used as both a co-oxidant and a source of hydroxyl groups. This protocol is thought to have potential to provide opportunities for chiral synthesis of 1/2,3-triols from corresponding allylic hydroperoxides in the absence of co-oxidant in one stage for the first time in the literature.

  首次利用催化剂OsO$_4}$和手性金鸡纳生物碱衍生物在丙酮-水混合物中实现了烯丙基过氧化氢官能团中的氧原子移除并重新引入双键，合成了对应的手性1/2,3-三醇，其对映选择性高达99% ee。过氧化氢基团既作为协同氧化剂，又作为羟基来源。这一方法被认为有望为从相应的烯丙基过氧化氢在无需协同氧化剂的情况下首度以一步法合成手性1/2,3-三醇提供可能。