(S)-(-)-2-1'-hydroxyethyl-3,4-dihydronaphthalene | 76888-37-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-(-)-2-1'-hydroxyethyl-3,4-dihydronaphthalene
• 英文别名: (1S)-1-(3,4-dihydronaphthalen-2-yl)ethanol
• CAS: 76888-37-4
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: NAJHDMJJXQBEPY-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  (S)-2-(1-(3,4-dihydronaphthalen-2-yl)ethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 双氧水 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 (S)-(-)-2-1'-hydroxyethyl-3,4-dihydronaphthalene
  参考文献：
  名称：

  通过氢化铜和钯双催化不对称制备 α-立体烯丙基硅烷、锗烷和硼酸酯的通用策略

  摘要：

  开发了一种对映选择性制备具有广泛官能团相容性的α-立体烯丙基类金属（M=B、Si、Ge）的通用方法。该方案采用 CuH 和 Pd 双重催化，从容易获得的乙烯基类金属和烯醇三氟甲磺酸酯中获得各种烯丙基类金属物质。

  DOI：

  10.1002/anie.202212630

文献信息

• Asymmetric reduction of αβ-unsaturated ketones with lithium aluminium hydride partially decomposed by (–)-N-methylephedrine and N-ethylaniline
  作者：Shiro Terashima、Norihiko Tanno、Kenji Koga

  DOI：10.1039/c39800001026

  日期：——

  The title asymmetric reaction is found to convert open chain enones into the corresponding optically active allylic alcohols in high optical (78–98% enantiomeric excess) and chemical (92–100%) yields.

  发现标题不对称反应可将开链烯酮转化为相应的旋光烯丙基醇，并具有较高的光学收率（对映体过量78-98％）和化学收率（92-100％）。
• Asymmetric reduction of various types of ketones with lithium aluminum hydride partially decomposed with (-)-N-methylephedrine and N-ethylaniline.
  作者：NORIHIKO TANNO、SHIRO TERASHIMA

  DOI：10.1248/cpb.31.837

  日期：——

  The asymmetric reduction of open chain enones to the corresponding optically active allylic alcohols was achieved in higher chemical (92-100%) and optical (78-98% e.e.) yields than those for cyclic enones (58-88% chemical and 34-58% optical yields). The observed high optical yields for optically active allylic alcohols can be explained on the assumption that, unlike cyclic enones in which the double bonds are fixed in s-trans conformation, open chain enones can be reduced in their s-cis conformations. An optically active propargylic alcohol was similarly produced from an ynone in 88% chemical and 76% optical yields by means of the present asymmetric reduction. When the same asymmetric reduction was applied to simple aromatic and aliphatic ketones by using 1.8 eq of the chiral reducing agent, the corresponding optically active alcohols were obtained in 88-100% chemical and 51-90% optical yields (for aromatic ketones) and in 78-98% chemical and 0-67% optical yields (for aliphatic ketones). On the basis of the results obtained in this and the preceding paper, a possible structure of the exploited chiral reducing agent is proposed and the transition states for the asymmetric reduction are discussed.

  开放链烯酮的不对称还原反应成功将其转化为相应的光学活性烯丙醇，化学产率（92-100%）和光学产率（78-98% e.e.)均高于环状烯酮（化学产率为58-88%，光学产率为34-58%）。相应的光学活性烯丙醇高的光学产率可以解释为，与固定在s-trans构象中的环状烯酮不同，开放链烯酮可以在其s-cis构象中进行还原。通过本不对称还原法，从一种炔酮中也成功获得了光学活性的丙炔醇，化学产率为88%，光学产率为76%。当对简单的芳香酮和脂肪酮应用相同的不对称还原，使用1.8倍当量的手性还原剂时，得到的相应光学活性醇的化学产率为88-100%（芳香酮）和78-98%（脂肪酮），光学产率分别为51-90%（芳香酮）和0-67%（脂肪酮）。基于本研究及前一篇论文中获得的结果，提出了所利用的手性还原剂的可能结构，并讨论了不对称还原的过渡态。
• TERASHIMA SHIRO; TANNO NORIHIKO; KOGA KENJI, J. CHEM. SOC. CHEM. COMMUN. 1980, NO 21, 1026-1027
  作者：TERASHIMA SHIRO、 TANNO NORIHIKO、 KOGA KENJI

  DOI：——

  日期：——
• TANNO, NORIHIKO;TERASHIMA, SHIRO, CHEM. AND PHARM. BULL., 1983, 31, N 3, 837-851
  作者：TANNO, NORIHIKO、TERASHIMA, SHIRO

  DOI：——

  日期：——