drimene | 86578-13-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: drimene
• 英文别名: drim-7(8)-ene；(4aS,8S,8aR)-4,4,7,8,8a-pentamethyl-1,2,3,4a,5,8-hexahydronaphthalene
• CAS: 86578-13-4
• 化学式: C₁₅H₂₆
• 分子量: 206.371
• InChiKey: IGSGDKBNFCVRCL-KCQAQPDRSA-N

物化性质

• 沸点：
  249.4±7.0 °C(Predicted)
• 密度：
  0.849±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  drimene 在 叔丁基过氧化氢 、 Co(dpm)₂ 、 苯硅烷 作用下， 以 正己烷 、 异丙醇 为溶剂， 以77%的产率得到(1S,2R,4aS,8aR)-1,2,5,5,8a-pentamethyl-1,2,3,4,4a,6,7,8-octahydronaphthalene
  参考文献：
  名称：

  Simple, Chemoselective Hydrogenation with Thermodynamic Stereocontrol

  摘要：

  Few methods permit the hydrogenation of alkenes to a thermodynamically favored configuration when steric effects dictate the alternative trajectory of hydrogen delivery. Dissolving metal reduction achieves this control, but with extremely low functional group tolerance. Here we demonstrate a catalytic hydrogenation of alkenes that affords the thermodynamic alkane products with remarkably broad functional group compatibility and rapid reaction rates at standard temperature and pressure.

  DOI：

  10.1021/ja412342g
• 作为产物：
  描述：

  (-)-补身醇 在 lithium aluminium tetrahydride 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.08h， 生成 drimene
  参考文献：
  名称：

  Simple, Chemoselective Hydrogenation with Thermodynamic Stereocontrol

  摘要：

  Few methods permit the hydrogenation of alkenes to a thermodynamically favored configuration when steric effects dictate the alternative trajectory of hydrogen delivery. Dissolving metal reduction achieves this control, but with extremely low functional group tolerance. Here we demonstrate a catalytic hydrogenation of alkenes that affords the thermodynamic alkane products with remarkably broad functional group compatibility and rapid reaction rates at standard temperature and pressure.

  DOI：

  10.1021/ja412342g

文献信息

• Chemo-enzymatic syntheses of drimane-type sesquiterpenes and the fundamental core of hongoquercin meroterpenoid by recombinant squalene–hopene cyclase
  作者：Yukie Yonemura、Takuro Ohyama、Tsutomu Hoshino

  DOI：10.1039/c1ob06419c

  日期：——

  Squalene–hopene cyclase (SHC) converts squalene (C30) into pentacyclic triterpenes of hopene and hopanol. A linear sesquiterpene, (6E,10E)-2,6,10-trimethyldodeca-2,6,10-triene, underwent cyclization catalyzed by SHC, affording the following six bicyclic sesquiterpenes (drimane skeleton) in relatively high yield (68%): drim-7(8)-ene, drim-8(12)-ene, drim-8(9)-ene, driman-8α-ol, driman-8β-ol, and the

  角鲨烯–希望 环化酶（SHC）转换 角鲨烯（C 30）成五环三萜希望 和 醇。线性倍半萜，（6 E，10 E）-2,6,10-三甲基十二烷基-2,6,10-三烯，经SHC催化环化，得到以下六个双环倍半萜烯（德里曼 骨架）相对较高的收率（68％）： drim-7（8）-烯， drim-8（12）-烯， drim-8（9）-烯，driman-8α-ol，driman-8β-ol和新的倍半萜烯，其名称为quasiclerodane，其骨架与双环戊二烯类似。为了扩大酶促合成的范围，对附加有酚部分的无环倍半萜进行SHC催化的酶促反应。成功制备了红槲皮素A和B中存在的环状美萜烯核心。的形成机理德里曼两种类型的倍半萜烯和红槲皮素A和B的环状金属萜烯核心。
• Stereochemical editing logic powered by the epimerization of unactivated tertiary stereocenters
  作者：Yu-An Zhang、Vignesh Palani、Alexander E. Seim、Yong Wang、Kathleen J. Wang、Alison E. Wendlandt

  DOI：10.1126/science.add6852

  日期：2022.10.28

  The stereoselective synthesis of complex targets requires the precise orchestration of chemical transformations that simultaneously establish the connectivity and spatial orientation of desired bonds. In this work, we describe a complementary paradigm for the synthesis of chiral molecules and their isomers, which tunes the three-dimensional structure of a molecule at a late stage. Key to the success

  复杂目标的立体选择性合成需要精确协调化学转化，同时建立所需键的连通性和空间方向。在这项工作中，我们描述了手性分子及其异构体合成的互补范例，该范例在后期调整分子的三维结构。该策略成功的关键是开发一种由十钨酸聚阴离子和二硫化物助催化剂组成的温和且高度通用的光催化方法，该方法能够使先前构型固定的未活化的三级立体异构中心相互转化。
• Simple, Chemoselective Hydrogenation with Thermodynamic Stereocontrol
  作者：Kotaro Iwasaki、Kanny K. Wan、Alberto Oppedisano、Steven W. M. Crossley、Ryan A. Shenvi

  DOI：10.1021/ja412342g

  日期：2014.1.29

  Few methods permit the hydrogenation of alkenes to a thermodynamically favored configuration when steric effects dictate the alternative trajectory of hydrogen delivery. Dissolving metal reduction achieves this control, but with extremely low functional group tolerance. Here we demonstrate a catalytic hydrogenation of alkenes that affords the thermodynamic alkane products with remarkably broad functional group compatibility and rapid reaction rates at standard temperature and pressure.