(1S,2S)-(1-methyl-2-vinyl-1,2-dihydronaphthyl)methan-1-ol | 114838-98-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: (1S,2S)-(1-methyl-2-vinyl-1,2-dihydronaphthyl)methan-1-ol
• 英文别名: (1S,2S)-2-ethenyl-1-methyl-2H-naphthalene-1-carbaldehyde
• CAS: 114838-98-1
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: BBXAUWBPDTYYSY-JSGCOSHPSA-N

物化性质

• 沸点：
  290.6±40.0 °C(predicted)
• 密度：
  1.130±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 草酸 、 三氟甲烷磺酸甲酯 作用下， 生成 (1S,2S)-(1-methyl-2-vinyl-1,2-dihydronaphthyl)methan-1-ol
  参考文献：
  名称：

  手性 1- 和 2- 取代萘的不对称串联加成。在(+)-叶绿素合成中的应用

  摘要：

  L'加成连续 d'烷基锂和 d'碘甲烷 a des（甲氧基甲基-4 [naphtyl-1 et 2]-2 phenyl-5） oxazolines-2 donne des [alkyl-2 dihydro-1,2methyl-1naphtyl-1 ]-2- 和 [烷基-1 二氢-1,2 甲基-2 萘基-2]-2 甲氧基甲基-4 苯基-5 恶唑啉-2

  DOI：

  10.1021/ja00222a021

文献信息

• A single-pot synthesis of 1,1,2-trisubstituted 1,2-dihydronaphthalenes in high enantiomeric purity
  作者：Mohamed K Mokhallalati、K.Raman Muralidharan、Lendon N Pridgen

  DOI：10.1016/s0040-4039(00)73330-2

  日期：1994.6

  followed by electrophilic trapping of the azaenolate is described. This tandem addition was performed in a single flask producing 1,1,2-trisubstituted 1,2-dihydronaphthalenes 7 in excellent yields and high enantioselectivities.

  描述了将格氏试剂非对映选择性地添加到非外消旋的2-（1-萘基）-4-（4R）-苯基-1,3-恶唑烷（1）中，然后亲电捕获氮杂烯酸酯。该串联添加在单个烧瓶中进行，该烧瓶以优异的产率和高对映选择性生产1,1,2-三取代的1,2-二氢萘7。
• Design, Synthesis, and Application of a <i>C</i>₂ Symmetric Chiral Ligand for Enantioselective Conjugate Addition of Organolithium to α,β-Unsaturated Aldimine
  作者：Mitsuru Shindo、Kenji Koga、Kiyoshi Tomioka

  DOI：10.1021/jo9813181

  日期：1998.12.1

  A C-2 symmetric chiral diether ligand, (1R,2R)-1,2-dimethoxy-1,2-diphenylethane was designed and synthesized on the basis of the concept of an asymmetric oxygen atom. Mediated by the chiral diether, high enantioselectivities were achieved in conjugate addition of organolithiums to naphthaldehyde imine and cyclic and acyclic alpha,beta-unsaturated aldimines. The absolute configuration of the product is predictable by the model.
• Asymmetric tandem additions to chiral naphthyloxazolines. A new and potent chiral auxiliary resulting in a major improvement in convenience and efficiency
  作者：David J. Rawson、A. I. Meyers

  DOI：10.1021/jo00007a010

  日期：1991.3

  Excellent diastereofacial selectivities over a wide range of temperatures (-78 to 25-degrees-C) were obtained with the title compounds with use of chiral oxazolines derived from (S)-valinol or (S)-tert-leucinol. These are the first useful levels of asymmetric induction observed without the presence of the chelating methoxyl groups. The dihydronaphthylcarbinols and aldehydes resulting from these additions were obtained in > 98% ee.
• Mokhallalati Mohamed K., Muralidharan K. Raman, Pridgen Lendon N., Tetrahedron Lett, 35 (1994) N 25, S 4267-4270
  作者：Mokhallalati Mohamed K., Muralidharan K. Raman, Pridgen Lendon N.

  DOI：——

  日期：——