Acetic acid (1S,4aR,6S,8aS)-6-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-ylmethyl ester | 856683-44-8

• 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: Acetic acid (1S,4aR,6S,8aS)-6-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-ylmethyl ester
• 英文别名: [(1S,4aR,6S,8aS)-6-[tert-butyl(dimethyl)silyl]oxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl acetate
• CAS: 856683-44-8
• 化学式: C₂₃H₄₂O₃Si
• 分子量: 394.67
• InChiKey: QUQYRZIQWUGKBN-IHFIDZABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.35
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,4aR,6S,8aS)-6-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-ylmethyl ester 在 二氯二茂钛 锰 、 lithium aluminium tetrahydride 、 四溴化碳 、 四丁基氟化铵 、 potassium carbonate 、 三苯基膦 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 20.5h， 生成 N-[4-[[4-[(5-乙基-1,3,4-噻二唑-2-基)氨基磺酰基]苯基]氨基磺酰基]苯基]乙酰胺
  参考文献：
  名称：

  Reductive Coupling of Terpenic Allylic Halides Catalyzed by Cp₂TiCl:  A Short and Efficient Asymmetric Synthesis of Onocerane Triterpenes

  摘要：

  Titanocene chloride catalyzes the regioselective alpha,alpha '-homocoupling of terpenic allylic halides. This process has been employed in the short and effective synthesis of terpenoids such as beta-onoceradiene (1), beta-onocerin (2), and squalene (3). Evidence is presented for eta(1)-allyltitanium species being involved in the coupling.

  DOI：

  10.1021/ol050335r
• 作为产物：
  描述：

  反,反-西基乙酸 在 二氯二茂钛 咪唑 、 2,3,6-三甲基吡啶 、 锰 、 三甲基氯硅烷 、 AD-mix-β 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 Acetic acid (1S,4aR,6S,8aS)-6-(tert-butyl-dimethyl-silanyloxy)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-ylmethyl ester
  参考文献：
  名称：

  Reductive Coupling of Terpenic Allylic Halides Catalyzed by Cp₂TiCl:  A Short and Efficient Asymmetric Synthesis of Onocerane Triterpenes

  摘要：

  Titanocene chloride catalyzes the regioselective alpha,alpha '-homocoupling of terpenic allylic halides. This process has been employed in the short and effective synthesis of terpenoids such as beta-onoceradiene (1), beta-onocerin (2), and squalene (3). Evidence is presented for eta(1)-allyltitanium species being involved in the coupling.

  DOI：

  10.1021/ol050335r

文献信息

• Enantioselective Total Synthesis of the Potent Anti-inflammatory (+)-Myrrhanol A
  作者：Victoriano Domingo、Lúcia Silva、Horacio R. Diéguez、Jesús F. Arteaga、José F. Quílez del Moral、Alejandro F. Barrero

  DOI：10.1021/jo901011m

  日期：2009.8.21

  The first total synthesis of potent anti-inflammatory polypodanes (+)-myrrhanol A (1), (+)-myrrhanone A (2), (+)-myrrhanone B (3), and (+)-myrrhanol B (4) has been achieved. Key steps in our convergent, highly stereocontrolled route are a Ti(III)-mediated radical cyclization of a chiral monoepoxide to furnish a bicyclic synthon that combines stereospecifically with an acyclic vinyl iodide via an intermolecular

  首次有效的抗炎性多足动物（+）-没药醇A（1），（+）-没药酮A（2），（+）-没药酮B（3）和（+）-没药醇B（4）的首次合成已经实现。在我们收敛的，高度立体受控的途径中的关键步骤是手性单环氧化物的Ti（III）介导的自由基环化，以提供双环合成子，该双环合成子通过分子间B-烷基Suzuki-Miyaura交叉偶联与无环乙烯基碘立体定向结合。
• Enantioselective synthesis of 3(S)-hydroxy polygodial derivatives and evaluation of their vanilloid activity
  作者：Mariantonietta D’Acunto、Carmela Della Monica、Irene Izzo、Luciano De Petrocellis、Vincenzo di Marzo、Aldo Spinella

  DOI：10.1016/j.tet.2010.11.002

  日期：2010.12

  The enantioselective synthesis of 3(S)-hydroxy polygodial and its acetyl derivative is described. The construction of the 3-hydroxy drimane skeleton was based on the titanium-catalyzed radical cyclization of (10S)-10, 11-epoxy-farnesyl acetate. Only underivatized 3(S)-hydroxy polygodial showed activity in assays on VR1 vanilloid receptor in HEK cells transfected with the human VR1. (C) 2010 Elsevier Ltd. All rights reserved.