[(E)-(R)-2-Azido-4-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-but-3-enyloxy]-tert-butyl-diphenyl-silane | 1042908-25-7

• 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: [(E)-(R)-2-Azido-4-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-but-3-enyloxy]-tert-butyl-diphenyl-silane
• 英文别名: [(E,2R)-2-azido-4-[(1S,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]but-3-enoxy]-tert-butyl-diphenylsilane
• CAS: 1042908-25-7
• 化学式: C₃₀H₄₃N₃OSi
• 分子量: 489.776
• InChiKey: MUNOOICIFARKFR-OHITWQCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.51
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(E)-(R)-2-Azido-4-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-but-3-enyloxy]-tert-butyl-diphenyl-silane 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 N-[(E)-(R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-3-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-allyl]-acrylamide
  参考文献：
  名称：

  Cleavage of a chiral auxiliary using RCM on an especially sterically crowded alkene: Syntheses of chiral carbo- and heterocycles

  摘要：

  Chiral 1,5-, 1,6-, and 1,7-dienes generated in 3-4 steps from chiral auxiliary p-menthane-3-carboxaldehyde undergo RCM with notable discrepancies in reactivity depending on the nature and number of substituents flanking the central double bond. The chiral auxiliary is thus cleaved releasing a carbo- or heterocycle in the process. Special features concerning the RCM on these especially crowded systems are discussed. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.07.028
• 作为产物：
  描述：

  (R,E)-4-((tert-butyldiphenylsilyl)oxy)-1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)but-2-en-1-ol 在 三(2-氯乙基)胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 以91%的产率得到[(E)-(R)-2-Azido-4-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-but-3-enyloxy]-tert-butyl-diphenyl-silane
  参考文献：
  名称：

  手性烯丙基叠氮化物的空间偏向3,3-Sigmatropic重排：在生物碱的总合成中的应用

  摘要：

  We describe a tandem Mitsunobu/3,3-sigmatropic rearrangement of allylic azides on a chiral auxiliary system that favors one regioisomer thanks to its exceptional steric bias. The sequence may be completed by the oxidative cleavage of the auxiliary or by a ring-closing metathesis reaction that produces a carboor heterocycle directly and a recyclable form of the chiral auxiliary. Applications of the methodology to the total synthesis of (+)-coniine, (+)-lentiginosin, and (+)-pumiliotoxin C are reported.

  DOI：

  10.1021/jo800817p