tert-Butyl-diphenyl-[3-((1S,6R)-1,2,6-trimethyl-cyclohex-2-enyl)-propoxy]-silane | 1027430-41-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-Butyl-diphenyl-[3-((1S,6R)-1,2,6-trimethyl-cyclohex-2-enyl)-propoxy]-silane
• 英文别名: tert-butyl-diphenyl-[3-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]propoxy]silane
• CAS: 1027430-41-6
• 化学式: C₂₈H₄₀OSi
• 分子量: 420.71
• InChiKey: ZTJRWMWOWQYVFI-UFHPHHKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.73
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-Butyl-diphenyl-[3-((1S,6R)-1,2,6-trimethyl-cyclohex-2-enyl)-propoxy]-silane 在 草酰氯 、 四丁基氟化铵 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.25h， 生成 3-((1S,6R)-1,2,6-Trimethyl-cyclohex-2-enyl)-propionaldehyde
  参考文献：
  名称：

  Synthesis of a homochiral ketone having a pinguisane skeleton using phenylethylamine as a chiral auxiliary: a formal total synthesis of deoxopinguisone

  摘要：

  A homochiral bicyclic ketone having a pinguisane skeleton has: been synthesised starting from homochiral methyl 3-[(1 'S,6 'R)-1 ' ,6 ' -dimethyl-2 ' -oxo-1-yl]propionate prepared from pulegone using phenylethylamine as a chiral auxiliary. The five-membered ring was constructed by the Hosomi-Sakurai reaction of the allylsilane derived from the ketone. This synthesis can be considered a formal synthesis of deoxopinguisone. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00041-6
• 作为产物：
  描述：

  3-((1S,2R)-1,2-Dimethyl-6-oxo-cyclohexyl)-propionic acid methyl ester 在 lithium aluminium tetrahydride 、 重铬酸吡啶 、 cerium(III) chloride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 167.0h， 生成 tert-Butyl-diphenyl-[3-((1S,6R)-1,2,6-trimethyl-cyclohex-2-enyl)-propoxy]-silane
  参考文献：
  名称：

  Synthesis of a homochiral ketone having a pinguisane skeleton using phenylethylamine as a chiral auxiliary: a formal total synthesis of deoxopinguisone

  摘要：

  A homochiral bicyclic ketone having a pinguisane skeleton has: been synthesised starting from homochiral methyl 3-[(1 'S,6 'R)-1 ' ,6 ' -dimethyl-2 ' -oxo-1-yl]propionate prepared from pulegone using phenylethylamine as a chiral auxiliary. The five-membered ring was constructed by the Hosomi-Sakurai reaction of the allylsilane derived from the ketone. This synthesis can be considered a formal synthesis of deoxopinguisone. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00041-6

文献信息

• Total Synthesis and Structure Revision of Halioxepine
  作者：Caroline Poock、Markus Kalesse

  DOI：10.1002/chem.202004847

  日期：2021.1.21

  total synthesis of halioxepine is accomplished using a 1,4‐addition for constructing the quaternary center at C10 and a halo etherification for the generation of the tertiary ether at C7. The correct structure of halioxepine was determined by assembling different enantiomeric building blocks and by changing the relative configuration between C10 and C15.

  卤氧杂环己烷的首次全合成是通过 1,4 加成在 C10 处构建四级中心和卤代醚化在 C7 处生成叔醚来完成的。通过组装不同的对映体结构单元并改变 C10 和 C15 之间的相对构型，确定了卤氧杂平的正确结构。
• Synthesis of a homochiral ketone having a pinguisane skeleton using phenylethylamine as a chiral auxiliary: a formal total synthesis of deoxopinguisone
  作者：Motoo Tori、Chiho Makino、Kenji Hisazumi、Masakazu Sono、Katsuyuki Nakashima

  DOI：10.1016/s0957-4166(01)00041-6

  日期：2001.2

  A homochiral bicyclic ketone having a pinguisane skeleton has: been synthesised starting from homochiral methyl 3-[(1 'S,6 'R)-1 ' ,6 ' -dimethyl-2 ' -oxo-1-yl]propionate prepared from pulegone using phenylethylamine as a chiral auxiliary. The five-membered ring was constructed by the Hosomi-Sakurai reaction of the allylsilane derived from the ketone. This synthesis can be considered a formal synthesis of deoxopinguisone. (C) 2001 Elsevier Science Ltd. All rights reserved.