(1R,2R,6S,8R)-4-(Dimethyl-phenyl-silanyl)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane | 612835-98-0

• 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,2R,6S,8R)-4-(Dimethyl-phenyl-silanyl)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane
• 英文别名: dimethyl-phenyl-[(1R,2R,6S,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]silane
• CAS: 612835-98-0
• 化学式: C₁₈H₂₇BO₂Si
• 分子量: 314.308
• InChiKey: HCFBXPRBNUEAFL-NYCLONFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1,2-丁二烯 、 (1R,2R,6S,8R)-4-(Dimethyl-phenyl-silanyl)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane 在 (C₅H₅)(allyl)Pd 、 (R)-Ph₂PC₁₀H₆C₁₀H₇ 作用下， 以 甲苯 为溶剂， 以92%的产率得到(1R,2R,3S,5R)-pinanediol (3S)-3-(dimethylphenylsilyl)buten-2-ylboronate
  参考文献：
  名称：

  Enantioface-Selective Palladium-Catalyzed Silaboration of Allenes via Double Asymmetric Induction

  摘要：

  Enantioenriched beta-borylallylsilanes were synthesized by palladium-catalyzed enantioface-selective addition of the silicon-boron bond to terminal allenes using a palladium catalyst possessing a chiral monodentate phosphine ligand. Use of a silylborane bearing a chiral auxiliary on the boron atom was beneficial to gain enantioface selectivities as high as 96% de.

  DOI：

  10.1021/ja0368958
• 作为产物：
  描述：

  (1R,2R,3S,5R)-(-)-2,3-蒎烷二醇 、 N-[chloro-[dimethyl(phenyl)silyl]boranyl]-N-ethylethanamine 以 正己烷 为溶剂， 反应 1.0h， 以77%的产率得到(1R,2R,6S,8R)-4-(Dimethyl-phenyl-silanyl)-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane
  参考文献：
  名称：

  Enantioface-Selective Palladium-Catalyzed Silaboration of Allenes via Double Asymmetric Induction

  摘要：

  Enantioenriched beta-borylallylsilanes were synthesized by palladium-catalyzed enantioface-selective addition of the silicon-boron bond to terminal allenes using a palladium catalyst possessing a chiral monodentate phosphine ligand. Use of a silylborane bearing a chiral auxiliary on the boron atom was beneficial to gain enantioface selectivities as high as 96% de.

  DOI：

  10.1021/ja0368958

文献信息

• Asymmetric Silaboration of Terminal Allenes Bearing α-Stereogenic Centers:  Stereoselection Based on “Reagent Control”
  作者：Toshimichi Ohmura、Michinori Suginome

  DOI：10.1021/ol060666j

  日期：2006.6.1

  A highly enantioface-selective silaboration of allenes having stereogenic centers at the alpha-positions of the double bonds has been achieved using a combination of a chiral silylborane(-)-2 and a chiral Pd/(R)-3 catalyst. The chiral reagent system efficiently controlled the stereochemistry of the new stereogenic centers even in the reactions of mismatched combinations.
• Enantioface-Selective Palladium-Catalyzed Silaboration of Allenes via Double Asymmetric Induction
  作者：Michinori Suginome、Toshimichi Ohmura、Yoshihiro Miyake、Shin'ichirou Mitani、Yoshihiko Ito、Masahiro Murakami

  DOI：10.1021/ja0368958

  日期：2003.9.1

  Enantioenriched beta-borylallylsilanes were synthesized by palladium-catalyzed enantioface-selective addition of the silicon-boron bond to terminal allenes using a palladium catalyst possessing a chiral monodentate phosphine ligand. Use of a silylborane bearing a chiral auxiliary on the boron atom was beneficial to gain enantioface selectivities as high as 96% de.