(4S)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-ol | 135557-18-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4S)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-ol
• 英文别名: (4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo[2.2.1]heptan-2-exo-ol；(1R,2S,3S,4R)-4,7,7-trimethyl-3-naphthalen-1-ylbicyclo[2.2.1]heptan-2-ol
• CAS: 135557-18-5
• 化学式: C₂₀H₂₄O
• 分子量: 280.41
• InChiKey: QWJIWXOLJZRJMC-CGBFIWBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4S)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-ol 在 4-二甲氨基吡啶 、 (5,10,15,20-tetraphenylporphyrinato)rhodium(III) chloride 对甲苯磺酰叠氮 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 (2R,3R)-1,7,7-trimethyl-2-(1-naphthyl)bicyclo<2.2.1>hept-3-yl (1S,5S)-2-oxobicyclo<3.1.0>hexane-1-carboxylate
  参考文献：
  名称：

  A new synthetic route to 1,25-dihydroxy-vitamin D3

  摘要：

  A synthesis of 1,25-dihydroxy-vitamin D3 using a new acetylenic Ring-A precursor is described. Ring-A synthons 4a or 4b can be prepared in homochiral form by a disastereoselective diazoester cyclization.

  DOI：

  10.1016/s0040-4039(00)79918-7
• 作为产物：
  描述：

  1-((1S,4S)-1,7,7-Trimethyl-bicyclo[2.2.1]hept-2-en-2-yl)-naphthalene 在 lithium aluminium tetrahydride 作用下， 生成 (4S)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-ol
  参考文献：
  名称：

  A new synthetic route to 1,25-dihydroxy-vitamin D3

  摘要：

  A synthesis of 1,25-dihydroxy-vitamin D3 using a new acetylenic Ring-A precursor is described. Ring-A synthons 4a or 4b can be prepared in homochiral form by a disastereoselective diazoester cyclization.

  DOI：

  10.1016/s0040-4039(00)79918-7

文献信息

• Optically active esters of 7-substituted 3,5-difunctionalized
  申请人：Sagami Chemical Research Center

  公开号：US05276154A1

  公开（公告）日：1994-01-04

  The present invention provides optically active esters of 7-substituted 3,5-difunctionalized 6-heptenoic acids represented by the following formula: ##STR1## wherein R is a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group or a substituted vinyl group; Ar is a condensed aromatic group; X.sup.1 and Y.sup.1 are not the same and each is a hydrogen atom or a hydroxyl group, or may be combined to represent an oxygen atom which forms a carbonyl group together with the carbon atom to which X.sup.1 and Y.sup.1 are attached; and X.sup.2 and Y.sup.2 are not the same and each is a hydrogen atom or a hydroxyl group, or may be combined to represent an oxygen atom which forms a carbonyl group together with the carbon atom to which X.sup.2 and Y.sup.2 are attached, or enantiomers thereof. The present invention further provides processes for preparing the above optically active esters and 7-substituted (3R, 5S, 6E)-3,5-dihydroxy-6-hepten-1,5-olides. These esters are useful as synthetic intermediates for preparing the above lactones having an inhibitory activity of HMG-CoA reductase as well as a sex attractant pheromone of beetles, endo-1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane.

  本发明提供了以下式子所示的7-取代3,5-二官能团6-庚烯酸的光学活性酯：##STR1## 其中R是取代或未取代的芳基、取代或未取代的杂环芳基或取代的乙烯基；Ar是缩合芳基；X1和Y1不相同，每个都是氢原子或羟基，或者可以结合在一起表示氧原子，与X1和Y1连接的碳原子形成羰基；X2和Y2不相同，每个都是氢原子或羟基，或者可以结合在一起表示氧原子，与X2和Y2连接的碳原子形成羰基，或其对映体。本发明还提供了制备上述光学活性酯和7-取代（3R，5S，6E）-3,5-二羟基-6-庚烯-1,5-内酯的方法。这些酯可用作合成中间体，用于制备具有HMG-CoA还原酶抑制活性以及甲虫的性引诱素内-1,3-二甲基-2,9-二氧杂双环[3.3.1]壬烷的上述内酯。
• The Rh2(OAc)4 catalysed CH insertion in chiral ester diazoanilides
  作者：Andrew G.H. Wee、Baosheng Liu

  DOI：10.1016/0040-4039(95)02115-9

  日期：1996.1

  The Rh2(OAc)4 -catalysed CH insertion reaction in chiral ester diazoanilides was investigated and was found to yield 4-substituted 2-pyrrolidinones with moderate to high e.e. (37–98 %) after decarbalkoxylation. Electronic effects were found to oppose steric effects in influencing the enantioselectivity of the reaction in N-arylethyl diazoanilides.

  研究了Rh 2（OAc）4催化的手性酯重氮苯胺化物中的CH插入反应，发现该化合物在脱碳烷氧基化后可产生具有中等至较高ee（37-98％）的4-取代的2-吡咯烷酮。发现在影响N-芳基乙基重氮苯胺中反应的对映选择性方面，电子效应与空间效应相反。
• Optically active esters of 7-substituted 3,5-difunctionalized 6-heptenoic acids
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP0475627A1

  公开（公告）日：1992-03-18

  An optically active ester of formula (I): wherein:    R is a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group or a substituted vinyl group;    Ar is a condensed aromatic group;    X¹ and Y¹ are not the same and each is a hydrogen atom or a hydroxyl group, or together represent an oxygen atom which forms a carbonyl group together with the carbon atom to which X¹ and Y¹ are attached; and    X² and Y² are not the same and each is a hydrogen atom or a hydroxyl group, or together represent an oxygen atom which forms a carbonyl group together with the carbon atom to which X² and Y² are attached, or an enantiomer thereof.

  化学式为（I）的光学活性酯，其中：R是取代或未取代的芳香基团，取代或未取代的杂环芳香基团或取代的乙烯基团；Ar是紧缩的芳香基团；X¹和Y¹不相同，每个都是氢原子或羟基，或者一起表示一个氧原子，该氧原子与X¹和Y¹连接的碳原子形成一个羰基基团；X²和Y²不相同，每个都是氢原子或羟基，或者一起表示一个氧原子，该氧原子与X²和Y²连接的碳原子形成一个羰基基团，或其对映异构体。
• TABER, D. F.;RAMAN, K., J. AMER. CHEM. SOC., 1983, 105, N 18, 5935-5937
  作者：TABER, D. F.、RAMAN, K.

  DOI：——

  日期：——
• US5276154A
  申请人：——

  公开号：US5276154A

  公开（公告）日：1994-01-04