(S)-(1-(naphthalen-2-ylmethyl)pyrrolidin-2-yl)methanol | 166803-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-(1-(naphthalen-2-ylmethyl)pyrrolidin-2-yl)methanol
• 英文别名: [(2S)-1-(2-naphthylmethyl)pyrrolidin-2-yl]methanol；(S)-N-(β-naphthyl)methyl-2-pyrrolidine methanol；(S)-N-(beta-naphthyl)methyl-2-pyrrolidine methanol；[(2S)-1-(naphthalen-2-ylmethyl)pyrrolidin-2-yl]methanol
• CAS: 166803-33-4
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: VNSNZINAEKIPFV-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(1-(naphthalen-2-ylmethyl)pyrrolidin-2-yl)methanol 、 碘甲烷 以 乙腈 为溶剂， 反应 24.0h， 以85%的产率得到(1S,2S)-2-Hydroxymethyl-1-methyl-1-naphthalen-2-ylmethyl-pyrrolidinium; iodide
  参考文献：
  名称：

  Revisiting optically active quaternary derivatives made from prolinol as phase transfer catalysts

  摘要：

  New non-racemic ammonium salts derived from prolinol have been prepared which are stereogenic both at N and at C. Absolute configurations rest on X-ray structures for 3c and 7a. The new compounds have been tested in a number of known enantioselective phase transfer catalytic (PTC) reactions to gain insight into steric control factors in such processes. Only very moderate e.e.s were observed. A SAMP hydrazone related catalyst (7a) reported by other authors was fully characterized. Racemic reaction products were obtained in two alkylations of diphenylmethylene benzylimine in the presence of this pure catalyst 7a. Very high e.e.s reported previously by others could not be reproduced. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00213-4
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以2.5 g的产率得到(S)-(1-(naphthalen-2-ylmethyl)pyrrolidin-2-yl)methanol
  参考文献：
  名称：

  化学计量量的脯氨酸衍生的 β-氨基醇促进末端炔烃与 N-（二苯基膦酰基）亚胺的不对称加成

  摘要：

  描述了一种用于制备光学活性炔丙胺的新合成方法。通过使用二乙基锌和脯氨酸衍生的 β-氨基醇研究了芳香族、杂芳香族、脂肪族和 α,β-不饱和 N-（二苯基膦酰基）亚胺的炔基化反应。N-(二苯基膦酰基)-保护的炔丙胺可以以高产率合成，并且具有良好到优异的对映选择性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900342
• 作为试剂：
  描述：

  N-亚苄基-P,P-二苯基次膦酸酰胺 、 2-甲基-1-丁烯-3-炔 在 diethylzinc 、 (S)-(1-(naphthalen-2-ylmethyl)pyrrolidin-2-yl)methanol 作用下， 以 二氯甲烷 为溶剂， 反应 55.0h， 生成 N-(4-methyl-1-phenylpent-4-en-2-ynyl)-P,P-diphenylphosphinic amide 、 N-(4-methyl-1-phenylpent-4-en-2-ynyl)-P,P-diphenylphosphinic amide
  参考文献：
  名称：

  化学计量量的脯氨酸衍生的 β-氨基醇促进末端炔烃与 N-（二苯基膦酰基）亚胺的不对称加成

  摘要：

  描述了一种用于制备光学活性炔丙胺的新合成方法。通过使用二乙基锌和脯氨酸衍生的 β-氨基醇研究了芳香族、杂芳香族、脂肪族和 α,β-不饱和 N-（二苯基膦酰基）亚胺的炔基化反应。N-(二苯基膦酰基)-保护的炔丙胺可以以高产率合成，并且具有良好到优异的对映选择性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900342

文献信息

• Optically active .beta.-aminoalkoxyborane complex
  申请人：Nissan Chemical Industries Ltd.

  公开号：US05663348A1

  公开（公告）日：1997-09-02

  An optically active .beta.-aminoalkoxyborane complex of the formula (I): ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.7 -C.sub.11 aralkyl or C.sub.6 -C.sub.10 aryl, R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl or C.sub.7 -C.sub.11 aralkyl, or R.sup.1 and R.sup.2 together form (CH.sub.2).sub.n wherein n is 3 or 4, and Ar is naphthyl, anthryl or phenanthryl, which may be substituted by from 1 to 3 substituents selected from the group consisting of halogen, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.7 -C.sub.11 aralkyl, C.sub.6 -C.sub.10 aryl, C.sub.1 -C.sub.6 alkoxy and styrene polymer substituents.

  化学式(I)的一种光学活性的.beta.-氨基烷氧基硼烷配合物：##STR1## 其中，R.sup.1是C.sub.1-C.sub.8烷基，C.sub.3-C.sub.7环烷基，C.sub.7-C.sub.11芳基烷基或C.sub.6-C.sub.10芳基；R.sup.2是氢，C.sub.1-C.sub.8烷基，C.sub.3-C.sub.7环烷基或C.sub.7-C.sub.11芳基烷基，或者R.sup.1和R.sup.2共同形成(CH.sub.2).sub.n，其中n为3或4；Ar是萘基，蒽基或菲基，可以被从1到3个取自卤素，硝基，C.sub.1-C.sub.6烷基，C.sub.3-C.sub.7环烷基，C.sub.2-C.sub.6烯基，C.sub.2-C.sub.6炔基，C.sub.7-C.sub.11芳基烷基，C.sub.6-C.sub.10芳基，C.sub.1-C.sub.6烷氧基和苯乙烯聚合物取代基的基团所取代。
• Optically active beta-aminoalkoxyborane complex
  申请人：Nissan Chemical Industries Ltd.

  公开号：US05808098A1

  公开（公告）日：1998-09-15

  1. An optically active .beta.-aminoalkoxyborane complex of the formula (I): ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.7 -C.sub.11 aralkyl or C.sub.6 -C.sub.10 aryl, R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl or C.sub.7 -C.sub.11 aralkyl, or R.sub.1 and R.sup.2 together form (CH.sub.2).sub.n wherein n is 3 or 4, and Ar is naphthyl, anthryl or phenanthryl, which may be substituted by from 1 to 3 substituents selected from the group consisting of halogen, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.7 -C.sub.11 aralkyl, C.sub.6 -C.sub.10 aryl, C.sub.1 -C.sub.6 alkoxy and styrene polymer substituents.

  一种光学活性的.beta.-氨基烷氧基硼烷配合物，化学式为(I)：##STR1##其中，R1为C1-C8烷基、C3-C7环烷基、C7-C11芳基烷基或C6-C10芳基；R2为氢、C1-C8烷基、C3-C7环烷基或C7-C11芳基烷基；或R1和R2共同形成(CH2)n，其中n为3或4；Ar为萘基、蒽基或菲基，可以被1至3个取代基所取代，所述取代基选自卤素、硝基、C1-C6烷基、C3-C7环烷基、C2-C6烯基、C2-C6炔基、C7-C11芳基烷基、C6-C10芳基、C1-C6烷氧基和苯乙烯聚合物取代基。
• Enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl)imines catalyzed by β-aminoalcohols with the prolinol skeleton
  作者：Raquel Almansa、David Guijarro、Miguel Yus

  DOI：10.1016/j.tetasy.2007.11.006

  日期：2007.11

  Several beta-aminoalcohols with the prolinol framework are shown to be very efficient catalysts for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl)imines. The use of 0.5 equiv of the catalyst leads to the expected addition products in good yields and with ee up to 94% in a reaction time of only 4 It at room temperature. This ee is the highest value reported so far using 0.5 equiv of an aminoalcohol as a promoter. High enantioselectivities are obtained in the addition of dialkylzincs to both aromatic and aliphatic imines. The amount of the catalyst can be reduced to 0.25 equiv with a slight decrease in the ee. A very interesting effect of the addition rate and temperature on the enantioselectivity was also observed. (c) 2007 Elsevier Ltd. All rights reserved.
• OPTICALLY ACTIVE BETA-AMINOALKOXYBORANE COMPLEXES
  申请人：NISSAN CHEMICAL INDUSTRIES, LIMITED

  公开号：EP0680484B1

  公开（公告）日：1998-08-19
• OPTICALLY ACTIVE $g(b)-AMINOALKOXYBORANE COMPLEX
  申请人：NISSAN CHEMICAL INDUSTRIES, LIMITED

  公开号：EP0680484A1

  公开（公告）日：1995-11-08