((1R,3aR,4S,6aS)-1,4-Dimethyl-1,3a,4,5,6,6a-hexahydro-pentalen-2-yloxy)-trimethyl-silane | 152377-57-6

• 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: ((1R,3aR,4S,6aS)-1,4-Dimethyl-1,3a,4,5,6,6a-hexahydro-pentalen-2-yloxy)-trimethyl-silane
• CAS: 152377-57-6
• 化学式: C₁₃H₂₄OSi
• 分子量: 224.418
• InChiKey: WCYZIHWKXZDMJV-IRCOFANPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  ((1R,3aR,4S,6aS)-1,4-Dimethyl-1,3a,4,5,6,6a-hexahydro-pentalen-2-yloxy)-trimethyl-silane 在 二甲基硫 、 臭氧 作用下， 生成 (4R,4aS,7S,7aR)-1-Hydroxy-4,7-dimethyl-hexahydro-cyclopenta[c]pyran-3-one
  参考文献：
  名称：

  Cyclopentenyllithium additions to chiral aldehydes. Diastereofacial selectivity indicating the absence of a pronounced neighboring carboxylate anion effect

  摘要：

  The 1,2-addition of cyclopentenyllithium to a series of three five-membered aldehydo esters and their hemiacylals has been examined in order to assess the level and direction of facial selectivity surrounding nucleophilic attack at the aldehyde carbonyl and to clarify possible electronic and steric contributions stemming from neighboring functional groups. Neither methyl substitution of the acetic acid (ester) side chain nor the interchange of ester for carboxylate anion serve as important diastereocontrol elements. Instead, diastereofacial selectivity in these and related cyclic carboxaldehydes is governed by the inherent structural features of the ring system to which the functional group is attached. The convenient preparation of a complete subset of isomerically pure bicyclic lactones carrying five stereogenic centers is reported.

  DOI：

  10.1021/jo00012a013
• 作为产物：
  描述：

  在 盐酸 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 镍 、 lithium diisopropyl amide 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 ((1R,3aR,4S,6aS)-1,4-Dimethyl-1,3a,4,5,6,6a-hexahydro-pentalen-2-yloxy)-trimethyl-silane
  参考文献：
  名称：

  New Asymmetric Syntheses of (-)-Isoiridomyrmecn and (+)-Loganin Aglucon 6-Acetate Utilizing C2-Symmetric Dimethyl 3,7-Dihydroxy-cis-bicyclo[3.3.0]octa-2,6-diene-2,6-dicarboxylate.

  摘要：

  (-)-异伊里多霉素的首次不对称合成和(-)-洛根素的首次全合成均使用手性C2对称结构单元3,7-二羟基-顺式-双环[3.3.0]辛烷-2,6-二烯-2,6-二羧酸二甲酯（2）进行，该结构单元由四甲基3,7-二氧代-顺式-双环-[3.3.0]辛烷-2,4,6,8-四羧酸（1）经脂肪酶催化不对称脱甲氧基羰基化反应制备而成。

  DOI：

  10.1248/cpb.46.736