(1R)-2c-Methyl-5c-isopropyl-(1rH)-bicyclo<3.1.0>hexan, (-)-Thujan B, (-)-cis-Thujan | 5523-90-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R)-2c-Methyl-5c-isopropyl-(1rH)-bicyclo<3.1.0>hexan, (-)-Thujan B, (-)-cis-Thujan
• 英文别名: (-)-cis-Thujan；(1R,4S)-thujane；(1R,4S)-Thujan；Gctnbvhdrfkllk-ivzwlzjfsa-；(1R,4S,5R)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexane
• CAS: 5523-90-0
• 化学式: C₁₀H₁₈
• 分子量: 138.253
• InChiKey: GCTNBVHDRFKLLK-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  α,β-侧柏酮 生成 (1R)-2c-Methyl-5c-isopropyl-(1rH)-bicyclo<3.1.0>hexan, (-)-Thujan B, (-)-cis-Thujan
  参考文献：
  名称：

  金钟柏的绝对配置

  摘要：

  （+）-顺式-和（+）-反-金钟柏（XIV和XV）已通过（+）-pulegene（XIII）与（+）-pulegone（IX）相关。使用立体定向反应，金钟柏系列的烃已与它们的氧化成员相连。Norin对这些物质发现的绝对构型与我们的发现相符。

  DOI：

  10.1016/0040-4020(66)80132-1

文献信息

• Modular Catalysts for Diene Cycloisomerization:  Rapid and Enantioselective Variants for Bicyclopropane Synthesis
  作者：Jeremy A. Feducia、Alison N. Campbell、Michael Q. Doherty、Michel R. Gagné

  DOI：10.1021/ja064335d

  日期：2006.10.1

  Deconstructing the tridentate (triphos)Pt(II) first-generation catalysts into mixed diphosphine/monophosphine combinations (P2P) has led to new, more active catalysts for the cycloisomerization of 1,6-, and 1,7-dienes into bicyclo-[3.1.0] and -[4.1.0] products. When the diphosphine was the small bite angle dppm, reaction rates were similar to 20-fold faster than with triphos, although reaction rates and diastereoselectivities were also sensitive to the monophosphine (PMe3 being optimal for rate, PPh3 being optimal for selectivity). When the diphosphine was xyl-BINAP or SEGPHOS, the catalysts were enantioselective, and enantio-ratios up to 98:2 were observed. Both sets of catalysts showed enhanced functional group tolerance in comparison to the original (triphos)Pt2+ catalyst. X-ray structures for both precatalysts are also reported.
• Hydroboration of terpenes. V. Isomerization of (+)-sabinene to (+)-.alpha.-thujene. Hydroboration of (+)-sabinene and (+).alpha.-thujene with configurational assignments for the thujanols
  作者：Shrinivas P. Acharya、Herbert Charles Brown、Akira Suzuki、Seichi Nozawa、Mitsuomi Itoh

  DOI：10.1021/jo01262a048

  日期：1969.10
• The absolute configuration of thujane
  作者：G. Ohloff、G. Uhde、A.F. Thomas、E.sz. Kováts

  DOI：10.1016/0040-4020(66)80132-1

  日期：1966.1

  (+)-cis- and (+)-trans-Thujane (XIV and XV) have been correlated with (+)-pulegone (IX) via (+)-pulegene (XIII). Using stereospecific reactions, the hydrocarbons of the thujane series have been linked with their oxygenated members. The absolute configurations found by Norin for these substances are in accord with our findings.

  （+）-顺式-和（+）-反-金钟柏（XIV和XV）已通过（+）-pulegene（XIII）与（+）-pulegone（IX）相关。使用立体定向反应，金钟柏系列的烃已与它们的氧化成员相连。Norin对这些物质发现的绝对构型与我们的发现相符。