6-<(tert-butyldimethylsilyl)oxy>cyclodecan-1-one | 144493-60-7

• 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: 6-<(tert-butyldimethylsilyl)oxy>cyclodecan-1-one
• 英文别名: 6-<(tert-Butyldimethylsilyl)oxy>cyclodecanone；6-(tert-butyl)dimethylsilyloxy-1-cyclodecanone；6-[Tert-butyl(dimethyl)silyl]oxycyclodecan-1-one
• CAS: 144493-60-7
• 化学式: C₁₆H₃₂O₂Si
• 分子量: 284.514
• InChiKey: MYVRUGXJTOFAFW-UHFFFAOYSA-N

物化性质

• 沸点：
  337.0±35.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-<(tert-butyldimethylsilyl)oxy>cyclodecan-1-one 在 magnesium 作用下， 生成 4-(6-hydroxycyclodecyl)butan-1-yl acetate
  参考文献：
  名称：

  Concerning attempts to synthesize out-bicyclo[4.4.4]tetradec-1-ene derivatives

  摘要：

  The keto aldehydes 4-[6-oxo-1-(tetrahydropyranyloxy)cyclodecyl]butanal (17), (E)-4-(6-oxocyclodec-1-enyl)butanal (24), and 4-(6-oxocyclodecylidene)butanal (7) have been synthesized. No bicyclo[4.4.4]tetradecadienes were found in the products from the zero-valent titanium reductive cyclization of compound 24. Instead, products arising from transannular reactions of the cyclodecyl ring system were isolated. 1,6-Divinylbicyclo[4.4.0]decane (32) was obtained from the reductive cyclization of keto enal 7. The most plausible route for its formation is through a Cope rearrangement of a bicyclo[4.4.4]tetradecene derivative, suggesting that an out-bicyclo[4.4.4]tetradecenylbistitanium pinacolate 8 intervened.

  DOI：

  10.1021/jo00052a024
• 作为产物：
  描述：

  1-<(tert-butyldimethylsilyl)oxy>cyclodecan-6-ol 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 6-<(tert-butyldimethylsilyl)oxy>cyclodecan-1-one
  参考文献：
  名称：

  PYRROLIDINE DERIVATIVE AND PROCESS FOR PRODUCING THE SAME

  摘要：

  揭示了一种吡咯烷衍生物，它是喹诺啉衍生物侧链的中间体，可用作角鲨烯合酶抑制剂，并公开了其生产方法。 所述吡咯烷衍生物（X）由以下式（X）表示（其中R1和R2分别表示羟基，C1-6烷氧基或类似物；R3表示氢原子，苄基或类似物）；或其盐或水合物：

  公开号：

  EP1375479A9

文献信息

• Electrophilic and radical transannular cyclizations of 5-cyclodecenone to give either hydronaphthalene or hydroazulene products
  作者：David Colclough、James B. White、William B. Smith、Yongliang Chu

  DOI：10.1021/jo00075a025

  日期：1993.11

  The transannular cyclizations of the E and Z double-bond isomers of 5-cyclodecenone were investigated in order to determine the regio- and stereochemical preferences of the unsubstituted ring system. Electrophilic cyclization of the E isomer under either protic or Lewis acid conditions led to hydronaphthalenols with a preference for the trans ring fusion, while the Z led to only cis-fused hydronaphthalenols. Cyclization of the ketyl radical generated from the ketone led exclusively to a cis-fused hydroazulenol, regardless of double-bond geometry, although the E isomer was considerably more reactive than the Z isomer. The stereochemistry of the ring fusion in the products from (E)-5-cyclodecenone can be rationalized by cyclization through its lowest energy conformations in which the carbonyl oxygen is anti to the alkene hydrogen at C6, leading to the trans-fused hydronaphthalenol, and syn to the alkene hydrogen at C5, leading to the cis-fused hydroazulenol. For (Z)-5-cyclodecenone, molecular mechanics calculations found two low energy conformations, only one of which brings the alkene and the carbonyl groups close enough for their reaction with each other. In this conformation, the alkene hydrogens at C5 and C6 are syn to the oxygen of the ketone, leading to a cis ring fusion regardless of whether 1,5- or 1,6-cyclization is observed. The difference in regiochemistry in radical versus electrophilic cyclizations is explicable on the basis of the differences in mechanism for the two reaction pathways. The radical cyclizations are kinetic in nature with the ketyl radical adding to the proximate C5 alkene carbon in a very exothermic step, akin to the cyclization of 1-hexenyl radicals. The stereochemistry of the acid-induced cyclizations can be explained through the intermedicacy of either nonclassical or contact ion pairs, the regiochemistry reflecting the greater stability of the hydronaphthalene ring system over the hydroazulene. A system of nomenclature for unambiguously labeling each of the low energy conformations of (E)-5-cyclodecenones is also proposed.
• PYRROLIDINE DERIVATIVE AND PROCESS FOR PRODUCING THE SAME
  申请人：Eisai Co., Ltd.

  公开号：EP1375479A9

  公开（公告）日：2004-04-14

  A pyrrolidine derivative, which is an intermediate for a quinuclidine derivate side chain useful as a squalene synthase inhibitor, and producing method thereof are disclosed. A pyrrolidine derivative (X) represented by the following formula (X) (wherein R1 and R2 each represents a hydroxy group, C1-6 alkoxy groups or the like; R3 represents a hydrogen atom, a benzyl group or the like); or a salt thereof or a hydrate thereof:

  揭示了一种吡咯烷衍生物，它是喹诺啉衍生物侧链的中间体，可用作角鲨烯合酶抑制剂，并公开了其生产方法。 所述吡咯烷衍生物（X）由以下式（X）表示（其中R1和R2分别表示羟基，C1-6烷氧基或类似物；R3表示氢原子，苄基或类似物）；或其盐或水合物：
• Concerning attempts to synthesize out-bicyclo[4.4.4]tetradec-1-ene derivatives
  作者：David P. G. Hamon、Guy Y. Krippner

  DOI：10.1021/jo00052a024

  日期：1992.12

  The keto aldehydes 4-[6-oxo-1-(tetrahydropyranyloxy)cyclodecyl]butanal (17), (E)-4-(6-oxocyclodec-1-enyl)butanal (24), and 4-(6-oxocyclodecylidene)butanal (7) have been synthesized. No bicyclo[4.4.4]tetradecadienes were found in the products from the zero-valent titanium reductive cyclization of compound 24. Instead, products arising from transannular reactions of the cyclodecyl ring system were isolated. 1,6-Divinylbicyclo[4.4.0]decane (32) was obtained from the reductive cyclization of keto enal 7. The most plausible route for its formation is through a Cope rearrangement of a bicyclo[4.4.4]tetradecene derivative, suggesting that an out-bicyclo[4.4.4]tetradecenylbistitanium pinacolate 8 intervened.