2-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxymethyl-3,4-dihydro-2H-naphthalen-1-one | 1107609-99-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxymethyl-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: (2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-(hydroxymethyl)-3,4-dihydronaphthalen-1-one
• CAS: 1107609-99-3
• 化学式: C₂₈H₃₂O₃Si
• 分子量: 444.646
• InChiKey: UMIAETLCBGKVGR-MUUNZHRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxymethyl-3,4-dihydro-2H-naphthalen-1-one 在 N-碘代丁二酰亚胺 、 四丁基氟化铵 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 生成 9-hydroxymethyl-11-oxatricyclo[7.2.1.0(2,7)]dodeca-2,4,6-trien-8-one
  参考文献：
  名称：

  2，2-二羟甲基-1-四氢萘酮通过碘环化的立体选择性去对称化，新型对映纯[6.6.5]三环骨架的合成和化学酶多样性的产生

  摘要：

  前手性2,2-双羟甲基-1-四氢萘酮衍生物与N-卤代琥珀酰胺的立体选择性卤环化作用提供了一种有趣的三​​环骨架，存在于许多天然存在的hasubanan生物碱中。通过使用母体外消旋化合物的酶促动力学拆分（EKR）合成对映体纯的三环支架。微生物酮还原酶（白地霉，黑曲霉和近平滑念珠菌）介导的立体选择性还原反应已经成功地用于这些对映体纯的三环支架其中，随后官能团操作，提供了新的环状框架。

  DOI：

  10.1002/adsc.201100088
• 作为产物：
  描述：

  乙酸乙烯酯 、 2-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxymethyl-3,4-dihydro-2H-naphthalen-1-one 在 CALB lipase 作用下， 生成 2-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxymethyl-3,4-dihydro-2H-naphthalen-1-one 、 acetic acid (S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl ester
  参考文献：
  名称：

  Asymmetric synthesis of aryl cyclitols based on 1,2,3,4-tetrahydronaphthalene scaffolds

  摘要：

  A series of aryl cyclitols based on a 1,2,3,4-tetrahydronaphthalene scaffold have been synthesized in a stereocontrolled manner. These cyclitols possess four contiguous stereocenters amongst which one is a quaternary stereocenter, which has been constructed by applying enzymatic kinetic resolution reaction. The remaining stereocenters have been created by substrate directed asymmetric dihydroxylation reaction and stereoselective keto-reduction process. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.02.009

文献信息

• Enantioselective enzymatic desymmetrization of prochiral 1,3-diols and enzymatic resolution of monoprotected 1,3-diols based on α-tetralone and related multifunctional scaffolds
  作者：Tridib Mahapatra、Tapas Das、Samik Nanda

  DOI：10.1016/j.tetasy.2008.10.024

  日期：2008.11

  Novel multifunctional chemotypes based on alpha-tetralone, alpha-indarione, and chromanone have been synthesized by a chemo-enzymatic approach by applying an enzymatic irreversible transesterification strategy. The scaffolds synthesized can be further elaborated with subsequent enzymatic as well as chemical transformations for the generation of new sets of structurally related organic molecules. (C) 2008 Elsevier Ltd. All rights reserved.
• Stereoselective Desymmetrization of 2,2-Bishydroxymethyl-1-tetralones by Iodocyclization, Synthesis of Novel Enantiopure [6.6.5] Tricyclic Framework and Chemoenzymatic Diversity Generation
  作者：Tridib Mahapatra、Navendu Jana、Samik Nanda

  DOI：10.1002/adsc.201100088

  日期：2011.8

  Stereoselective halocyclization of pro-chiral 2,2-bishydroxymethyl-1-tetralone derivatives with N-halosuccinamides afforded an interesting tricyclic scaffold found in many naturally occurring hasubanan alkaloids. Enantiopure tricyclic scaffolds are synthesized by using enzymatic kinetic resolution (EKR) of the parent racemic compound. Microbial ketoreductase (Geotrichum candidum, Aspergillus niger

  前手性2,2-双羟甲基-1-四氢萘酮衍生物与N-卤代琥珀酰胺的立体选择性卤环化作用提供了一种有趣的三​​环骨架，存在于许多天然存在的hasubanan生物碱中。通过使用母体外消旋化合物的酶促动力学拆分（EKR）合成对映体纯的三环支架。微生物酮还原酶（白地霉，黑曲霉和近平滑念珠菌）介导的立体选择性还原反应已经成功地用于这些对映体纯的三环支架其中，随后官能团操作，提供了新的环状框架。
• Asymmetric synthesis of aryl cyclitols based on 1,2,3,4-tetrahydronaphthalene scaffolds
  作者：Tridib Mahapatra、Samik Nanda

  DOI：10.1016/j.tetasy.2011.02.009

  日期：2011.2

  A series of aryl cyclitols based on a 1,2,3,4-tetrahydronaphthalene scaffold have been synthesized in a stereocontrolled manner. These cyclitols possess four contiguous stereocenters amongst which one is a quaternary stereocenter, which has been constructed by applying enzymatic kinetic resolution reaction. The remaining stereocenters have been created by substrate directed asymmetric dihydroxylation reaction and stereoselective keto-reduction process. (C) 2011 Elsevier Ltd. All rights reserved.