(2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-one | 131691-33-3

• 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: (2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-one
• 英文别名: 2S-(1'-t-butyldimethylsilyloxy-2'R-propyl)-5R-methylcyclohexanone；(2S,5R)-2-[(2R)-1-[tert-butyl(dimethyl)silyl]oxypropan-2-yl]-5-methylcyclohexan-1-one
• CAS: 131691-33-3
• 化学式: C₁₆H₃₂O₂Si
• 分子量: 284.514
• InChiKey: ORRQCQWLDNXVET-RDBSUJKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  19
• 可旋转键数：
  5
• 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

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-6-(1,3-dithian-2-ylidene)-5-methylcyclohexan-1-one	1446428-36-9	C20H36O2S2Si	400.722

反应信息

• 作为反应物：
  描述：

  (2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-one 在 三氟化硼乙醚 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2-(R)-(1S,4R,5-methoxy-7-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)-propan-1-ol
  参考文献：
  名称：

  Total synthesis and structural confirmation of the antibacterial diterpene leubethanol

  摘要：

  We report the total synthesis of leubethanol (1), a serrulatane compound that has recently been reported as having considerable antibacterial activity against multidrug-resistant bacteria, such as Staphylococcus aureus, and is of interest for applications in the control of bacterial biofilms in human medicine. Our synthetic route begins with (-)-isopulegol (4) and key steps include substrate directed hydroboration to generate the C1' stereocentre and formation of the aromatic ring via the alpha-oxoketene-S,S-acetal intermediate 3. Overall the conversion of (-)-isopulegol (4) to leubethanol was achieved in 13 steps and an overall yield of 7%. Comparison of our spectroscopic data with those reported for leubethanol (1), isolated from Leucophyllum frutescens, verified the structure of the natural product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.082
• 作为产物：
  描述：

  异胡薄荷醇 在 4-二甲氨基吡啶 、 sodium hydroxide 、 草酰氯 、 双氧水 、 二甲基亚砜 、 三乙胺 、 diborane(6) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-one
  参考文献：
  名称：

  青蒿素的三环类似物：（+）-4,5-secoartemisinin和（–）-5-nor-4,5-secoartemisinin的合成和抗疟活性

  摘要：

  已合成了天然产物青蒿素的两个A环切割类似物，并检查了其体外抗疟活性。

  DOI：

  10.1039/c39900001487

文献信息

• Synthesis, conformational analysis, and antimalarial activity of tricyclic analogs of artemisinin
  作者：Mitchell A Avery、Fenglan Gao、Wesley K.M Chong、Thomas F Hendrickson、Wayne D Inman、Phillip Crews

  DOI：10.1016/s0040-4020(01)80810-3

  日期：1994.1

  Aspects of synthesis, conformational analysis, and antimalarial activity of artemisinin analogs (±)-5-nor-6-desmethyl-4,5-secoartemisinin (2), (−)-5-nor-4,5-secoartemisinin (3), (+)-4,5-secoartemisinin (4), and (+)-4,5-desethano-artemisinin (5)22 are described. The conformations of these multicyclic structures were determined through a combination of X-ray crystallography, NMR, and computational analysis

  青蒿素类似物（±）-5-nor-6-desmethyl-4,5-secoartemisinin（2），（-）-5-nor-4,5-secoartemisinin（3）的合成，构象分析和抗疟活性记载了（+）-4，5-半胱氨酸青蒿素（4）和（+）-4，5-脱乙氨基青蒿素（5）22。这些多环结构的构象是通过X射线晶体学，NMR和计算分析相结合来确定的，重点放在1,2,4-三恶烷的几何形状上。发现了2和3的两个主要解决方案构型：所有椅子形式2a和3a，以及扭曲船/扭曲船/椅子形式2b和3b分别。主溶液构象剂2a与通过X射线晶体学发现的固态结构匹配。计算表明（+）-4,5-Secoartemisinin（4）具有三个相等能量的构象：椅子/扭曲船4a，扭曲船/扭曲船/椅子4b，对应于X射线晶体结构和4c扭船/椅子/椅子。1,2,4-三恶烷环和内酯环在2b，3b，4a和4c中采用扭转舟构象。与青蒿素相比
• AVERY, MITCHELL A.;CHONG, WESLEY K. M.;BUPP, JAMES E., J. CHEM. SOC. CHEM. COMMUN.,(1990) N1, C. 1487-1489
  作者：AVERY, MITCHELL A.、CHONG, WESLEY K. M.、BUPP, JAMES E.

  DOI：——

  日期：——
• Tricyclic analogues of artemisinin: synthesis and antimalarial activity of (+)-4,5-secoartemisinin and (–)-5-nor-4,5-secoartemisinin
  作者：Mitchell A. Avery、Wesley K. M. Chong、James E. Bupp

  DOI：10.1039/c39900001487

  日期：——

  Two ring-A cleaved analogues of the natural product artemisinin have been synthesized and examined for in vitro antimalarial activity.

  已合成了天然产物青蒿素的两个A环切割类似物，并检查了其体外抗疟活性。
• Total synthesis and structural confirmation of the antibacterial diterpene leubethanol
  作者：Jessica M.H. Lu、Michael V. Perkins、Hans J. Griesser

  DOI：10.1016/j.tet.2013.05.082

  日期：2013.8

  We report the total synthesis of leubethanol (1), a serrulatane compound that has recently been reported as having considerable antibacterial activity against multidrug-resistant bacteria, such as Staphylococcus aureus, and is of interest for applications in the control of bacterial biofilms in human medicine. Our synthetic route begins with (-)-isopulegol (4) and key steps include substrate directed hydroboration to generate the C1' stereocentre and formation of the aromatic ring via the alpha-oxoketene-S,S-acetal intermediate 3. Overall the conversion of (-)-isopulegol (4) to leubethanol was achieved in 13 steps and an overall yield of 7%. Comparison of our spectroscopic data with those reported for leubethanol (1), isolated from Leucophyllum frutescens, verified the structure of the natural product. (C) 2013 Elsevier Ltd. All rights reserved.