(2E,7E)-2,5,5,8-tetramethyl-9-(t-butyldiphenylsilyloxy)-2,7-nonadien-1-ol | 184833-17-8

• 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: (2E,7E)-2,5,5,8-tetramethyl-9-(t-butyldiphenylsilyloxy)-2,7-nonadien-1-ol
• 英文别名: (2E,7E)-9-[tert-butyl(diphenyl)silyl]oxy-2,5,5,8-tetramethylnona-2,7-dien-1-ol
• CAS: 184833-17-8
• 化学式: C₂₉H₄₂O₂Si
• 分子量: 450.737
• InChiKey: OUIRDUUISHQELD-SIHVKLMXSA-N

物化性质

• 沸点：
  516.3±50.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.25
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,7E)-2,5,5,8-tetramethyl-9-(t-butyldiphenylsilyloxy)-2,7-nonadien-1-ol 在 重铬酸吡啶 、 乙二醇二甲醚 、 4 A molecular sieve 、 Celite 、 diethylzinc 作用下， 以 二氯甲烷 为溶剂， 反应 17.75h， 生成 (2S,3S,7E)-2,5,5,8-tetramethyl-2,3-methano-9-(t-butyldiphenylsilyloxy)-7-nonen-1-al
  参考文献：
  名称：

  Application of the chemo- and enantioselective cyclopropanation of polyenes to the total synthesis of (+)-bicyclohumulenone

  摘要：

  The chemo- and enantioselective cyclopropanation of a monoprotected bis(allylic alcohol) using a chiral dioxaborolane-derived ligand and Zn(CH2I)(2) was used as a key step in the total synthesis of (+)-bicyclohumulenone. The synthesis of this important perfume component was efficiently accomplished in 16 steps from diethyl 3,3-dimethylglutarate in 9% overall yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01014-4
• 作为产物：
  描述：

  3,3-dimethylglutaraldehyde 在 咪唑 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 32.25h， 生成 (2E,7E)-2,5,5,8-tetramethyl-9-(t-butyldiphenylsilyloxy)-2,7-nonadien-1-ol
  参考文献：
  名称：

  Application of the chemo- and enantioselective cyclopropanation of polyenes to the total synthesis of (+)-bicyclohumulenone

  摘要：

  The chemo- and enantioselective cyclopropanation of a monoprotected bis(allylic alcohol) using a chiral dioxaborolane-derived ligand and Zn(CH2I)(2) was used as a key step in the total synthesis of (+)-bicyclohumulenone. The synthesis of this important perfume component was efficiently accomplished in 16 steps from diethyl 3,3-dimethylglutarate in 9% overall yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01014-4

文献信息

• The chemo- and enantioselective cyclopropanation of polyenes: chiral auxiliary vs chiral reagent-based approach
  作者：AndréB. Charette、Hélène Juteau、Hélène Lebel、Denis Deschênes

  DOI：10.1016/0040-4039(96)01798-4

  日期：1996.10

  The chemo- and enantioselective cyclopropanation of allylic alcohols containing additional olefins was investigated using the dioxaborolane-derived reagent. High chemo- and enantioselectivities were usually observed if a mixture of the chiral dioxaborolane ligand/allylic alcohol was treated with a solution of Zn(CH2I)2·DME complex.

  使用衍生自二氧杂硼烷的试剂研究了含有其他烯烃的烯丙基醇的化学和对映选择性环丙烷化。如果将手性二氧杂硼烷配体/烯丙醇的混合物用Zn（CH 2 I）2 · DME络合物溶液处理，通常观察到较高的化学和对映选择性。
• Application of the chemo- and enantioselective cyclopropanation of polyenes to the total synthesis of (+)-bicyclohumulenone
  作者：AndréB. Charette、Hélène Juteau

  DOI：10.1016/s0040-4020(97)01014-4

  日期：1997.12

  The chemo- and enantioselective cyclopropanation of a monoprotected bis(allylic alcohol) using a chiral dioxaborolane-derived ligand and Zn(CH2I)(2) was used as a key step in the total synthesis of (+)-bicyclohumulenone. The synthesis of this important perfume component was efficiently accomplished in 16 steps from diethyl 3,3-dimethylglutarate in 9% overall yield. (C) 1997 Elsevier Science Ltd.