(1R,2S)-(+)-trans-1-(Hydroxymethyl)-2-phenyl-1,2-dihydronaphthalene | 99797-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2S)-(+)-trans-1-(Hydroxymethyl)-2-phenyl-1,2-dihydronaphthalene
• 英文别名: (+)-trans-1-(hydroxymethyl)-2-phenyl-1,2-dihydronaphthalene；(1R,2S)-(2-phenyl-1,2-dihydronaphthyl)methan-1-ol；[(1R,2S)-2-phenyl-1,2-dihydronaphthalen-1-yl]methanol
• CAS: 99797-48-5
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: MHKPLPOLWXKKKA-SJORKVTESA-N

物化性质

• 沸点：
  378.3±21.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (4R)-2-(1-萘基)-4-苯基-1,3-恶唑烷 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 (1R,2S)-(+)-trans-1-(Hydroxymethyl)-2-phenyl-1,2-dihydronaphthalene
  参考文献：
  名称：

  1,2- vs. 1,4-addition of nucleophilic organometallics to nonracemic 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines

  摘要：

  We herein report our results where the addition of organomagnesium reagents to 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidines occurred consistently in a 1,4-conjugate manner, while lithium, cerium, and copper organometallic reagents added in a 1,2-fashion. The 1,4-conjugate addition pathway was primarily exploited by using (4R)-2-(1-naphthyl)-4-phenyl-1,3-oxazolidine (4) as a substrate to obtain, after NaBH4 reduction of the intermediate aldehyde, trans-disubstituted 1,2-dihydronaphthalenes with enantiomeric excesses of 93-94%. The amino alcohol products resulting from 1,2-addition were oxidatively cleaved to afford enantiomeric enriched (R)-alpha-(1-naphthyl)alkylamines 6a and 6b in > 99% ee.

  DOI：

  10.1021/jo00030a035

文献信息

• Asymmetric addition of aryllithiums to naphthalene bha-esters catalyzed by a chiral ligand
  作者：Mitsuru Shindo、Kenji Koga

  DOI：10.1016/s0040-4039(00)61651-9

  日期：1993.1

  In the Presence of both stoichiometric and catalytic amounts of a chiral dieter 1, aryllithiums reacted with BHA-esters of naphthalenecarboxylic acids 2, 5 to afford the corresponding adducts 4, 6 in high ee.

  在这两种化学计量和催化量的手性减肥者的存在1，芳基锂与萘羧酸BHA-酯反应2，5，得到相应加合物4，6中的高ee值。
• Asymmetric additions to chiral naphthalenes. III. The synthesis of (+)-trans-1,2-disubstituted-1,2-dihydronaphthalenes
  作者：A. I. Meyers、Bruce A. Barner

  DOI：10.1021/jo00351a034

  日期：1986.1
• 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.
• Novel strategy of using a C2 symmetric chiral diether in the enantioselective conjugate addition of an organolithium to an .alpha.,.beta.-unsaturated aldimine
  作者：Kiyoshi Tomioka、Mitsuru Shindo、Kenji Koga

  DOI：10.1021/ja00203a032

  日期：1989.10
• TOMOIOKA, KIYOSHI;SHINDO, MITSURU;KOGA, KENJI, J. AMER. CHEM. SOC., 111,(1989) N1, C. 8266-8268
  作者：TOMOIOKA, KIYOSHI、SHINDO, MITSURU、KOGA, KENJI

  DOI：——

  日期：——