((2S,3S)-3-(naphthalen-1-yl)oxiran-2-yl)methanol | 192125-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ((2S,3S)-3-(naphthalen-1-yl)oxiran-2-yl)methanol
• 英文别名: (2S,3S)-3-(1-naphthyl)-2,3-epoxypropan-1-ol；(2S,3S)-2,3-epoxy-3-(1-naphthyl)propanol；3-(1-naphthyl)-2.3-epoxyallyl alcohol；[(2S,3S)-3-naphthalen-1-yloxiran-2-yl]methanol
• CAS: 192125-26-1
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: OTZIGYCHUSCIGQ-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((2S,3S)-3-(naphthalen-1-yl)oxiran-2-yl)methanol 在 palladium dihydroxide titanium(IV) isopropylate 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 51.0h， 生成 (2R,3R)-3-(tert-butoxycarbonylamino)-3-(1-naphthyl)-1,2-propanediol
  参考文献：
  名称：

  Enantioselective synthesis of N-Boc-1-naphthylglycine

  摘要：

  A new stereoselective synthesis of enantiomerically pure 1-naphthylglycine has been developed. The source of chirality is the catalytic Sharpless epoxidation. Regioselective and stereospecific ring-opening of the corresponding epoxy alcohol is performed either with sodium azide or with benzhydrylamine as ammonia synthetic equivalents. Subsequent hydrogenation in the presence of (Boc)(2)O affords crystalline N-Boc-3-(1-naphthyl)propane-1,2-diol which is enantiomerically enriched up to 100% ee and oxidized to the alpha-amino acid. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00137-7
• 作为产物：
  描述：

  (E)-ethyl 3-(naphthalen-1-yl)acrylate 在 二异丁基氢化铝 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 74.0h， 生成 ((2S,3S)-3-(naphthalen-1-yl)oxiran-2-yl)methanol
  参考文献：
  名称：

  Enantioselective epoxidation of tertiary allylic alcohols by chiral dihydroperoxides

  摘要：

  gem-Dihydroperoxides were successfully used for the enantioselective epoxidation of tertiary and primary allylic alcohols. Epoxides derived from tertiary alcohols were obtained in yields up to 71% with ee's up to 52%. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.032

文献信息

• Modular Bis(oxazoline) Ligands for Palladium Catalyzed Allylic Alkylation: Unprecedented Conformational Behaviour of a Bis(oxazoline) Palladium 3-1,3-Diphenylallyl Complex
  作者：Miquel Angel Pericàs、Cristina Puigjaner、Antoni Riera、Anton Vidal-Ferran、Montserrat Gómez、Francisco Jiménez、Guillermo Muller、Mercè Rocamora

  DOI：10.1002/1521-3765(20020916)8:18<4164::aid-chem4164>3.0.co;2-g

  日期：2002.9.16

  5-cis (6 c) stereochemistry at the individual rings have been prepared in high yield. Their eta(3)-allyl palladium complexes (8 a-g, 9 c and 10) have been used as catalytic precursors in allylic alkylation reactions with excellent enantioselectivities (up to 96 %) for the trans oxazoline derivatives, while Pd/6 c system was inactive. NMR studies on palladium eta(3)-1,3-diphenylallyl intermediates (11

  高产率地制备了在各个环上具有4,5-反式（5 ag）或4,5-顺式（6 c）立体化学的新对映体双（恶唑啉）家族。他们的eta（3）-烯丙基钯配合物（8 ag，9 c和10）已被用作烯丙基烷基化反应的催化前体，对恶唑啉衍生物具有出色的对映选择性（最高96％），而Pd / 6 c体系为不活跃。对钯eta（3）-1,3-二苯基烯丙基中间体（11a，c和e）的NMR研究表明，溶液中存在syn / syn-和syn / anti-烯丙基异构体。这类似于包含衍生自丙二酸的双（恶唑啉）的Pd烯丙基络合物中eta（3）-eta（1）-eta（3）异构的第一个例子。
• Prompt Determination of Absolute Configuration for Epoxy Alcohols via Exciton Chirality Protocol
  作者：Xiaoyong Li、Babak Borhan

  DOI：10.1021/ja805058t

  日期：2008.12.3

  A microscale protocol for determination of absolute configurations of 2,3-epoxy alcohols is described. 2,3-Disubstituted (cis and trans), 2,2-disubstituted, 2,2,3-trisubstituted, and 2,3,3-trisubstituted epoxy alcohols rendered prominent ECCD signals upon complexing with a Lewis acidic porphyrin tweezer and consequently provide straightforward assignment of chirality for epoxy alcohols. This method

  描述了用于确定 2,3-环氧醇绝对配置的微型协议。2,3-二取代（顺式和反式）、2,2-二取代、2,2,3-三取代和 2,3,3-三取代环氧醇在与路易斯酸性卟啉镊子复合后呈现显着的 ECCD 信号，从而提供环氧醇手性的直接分配。事实证明，对于上面列出的分子类别，该方法快速、简单、灵敏且可靠。
• Asymmetric epoxidation of α,β-unsaturated aldehydes catalyzed by a spiro-pyrrolidine-derived organocatalyst
  作者：Ming-Hui Xu、Yong-Qiang Tu、Jin-Miao Tian、Fu-Min Zhang、Shao-Hua Wang、Shi-Heng Zhang、Xiao-Ming Zhang

  DOI：10.1016/j.tetasy.2016.02.009

  日期：2016.4

  The asymmetric epoxidation of alpha,beta-unsaturated aldehydes, catalyzed by a spiro-pyrrolidine (SPD)-derived organocatalyst, has been accomplished with good diastereoselectivities (up to dr >20:1) and with high to excellent enantioselectivities (up to 99% ee). (C) 2016 Elsevier Ltd. All rights reserved.