(S)-4-(1-naphthalenyl)-3-buten-2-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-4-(1-naphthalenyl)-3-buten-2-ol
• 英文别名: (S)-(E)-4-(1-naphthyl)-3-buten-2-ol；(2S,3E)-4-(naphthalen-1-yl)-3-buten-2-ol；(2S,3E)-4-(1-naphthyl)-3-buten-2-ol；(E,2S)-4-naphthalen-1-ylbut-3-en-2-ol
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: KSZNZVNVDGKNOP-USKTWTLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  (E)-4-(1-萘基)-3-丁烯-2-酮 在 4-iodophenoxyborane 、 (S)-5-(bis(3,5-dimethylphenyl)(hydroxy)methyl)pyrrolidin-2-one 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 (R)-4-(1-naphthalenyl)-3-buten-2-ol 、 (S)-4-(1-naphthalenyl)-3-buten-2-ol
  参考文献：
  名称：

  使用由手性内酰胺醇原位生成的恶唑硼烷催化剂对映体选择性还原α，β-烯酮

  摘要：

  发现由手性内酰胺醇3和4-碘苯氧基硼烷原位制备的恶唑硼烷催化剂在-40℃下以高达90％ee的高对映选择性催化α，β-烯酮的对映选择性还原。

  DOI：

  10.1016/j.tetasy.2011.10.018

文献信息

• Aminocyclopentadienyl Ruthenium Complexes as Racemization Catalysts for Dynamic Kinetic Resolution of Secondary Alcohols at Ambient Temperature
  作者：Jun Ho Choi、Yoon Kyung Choi、Yu Hwan Kim、Eun Sil Park、Eun Jung Kim、Mahn-Joo Kim、Jaiwook Park

  DOI：10.1021/jo0355799

  日期：2004.3.1

  tests in the racemization of (S)-4-phenyl-2-butanol showed that 7 is the most active catalyst, although the difference decreased in the DKR. Complex 4 was used in the DKR of various alcohols; at room temperature, not only simple alcohols but also functionalized ones such as allylic alcohols, alkynyl alcohols, diols, hydroxyl esters, and chlorohydrins were successfully transformed to chiral acetates. In

  Aminocyclopentadienyl钌复合物，其可以用作常温消旋催化剂与在动态动力学拆分仲醇的（DKR），脂肪酶是从环戊-2,4- dienimines合成的Ru 3（CO）12，和CHCl 3： [2,3,4,5-PH 4（η 5 -C 4 CNHR）]的Ru（CO）2 Cl（上4：R =我-Pr; 5：R = ñ -Pr; 6：R =吨-Bu ），[2,5-ME 2 -3,4--PH 2（η 5 -C 4 CNHR）]的Ru（CO）2 Cl（上7：R = i -Pr; 8：R = PH），和[2,3,4,5-PH 4（η 5 -C 4 CNHAr）]的Ru（CO）2 Cl（上9：Ar为p -NO 2 ç 6 ħ 4 ; 10： Ar ＝p- ClC 6 H 4；11：Ar ＝ Ph；12：Ar ＝p- OMeC 6 H 4；13：Ar ＝p- NMe 2 C 6 H 4）。外消旋
• One-pot synthesis and resolution of chiral allylic alcohols
  作者：Ahmed Kamal、Mahendra Sandbhor、Ahmad Ali Shaik、V. Sravanthi

  DOI：10.1016/s0957-4166(03)00598-6

  日期：2003.9

  Substituted alpha,beta-unsaturated ketones were selectively reduced to the corresponding allylic alcohols under mild reaction conditions. The allylic alcohols thus obtained were kinetically resolved by lipase catalyzed transesterification in the same pot to afford chiral allylic alcohols in excellent enantioselectivity. Various lipases were screened for this one-pot transesterification of allylic alcohols. Effects of different solvent have also been studied under these conditions. Pseudomonas cepacia lipase immobilized on ceramic particles (PS-C) and on diatomaceous earth (PS-D) catalyzes this transesterification in diisopropyl ether in a highly efficient manner. (C) 2003 Elsevier Ltd. All rights reserved.
• Enantiomerically pure allylic alcohols: preparation by Candida parapsilosis ATCC 7330 mediated deracemisation
  作者：Devamani Titu、Anju Chadha

  DOI：10.1016/j.tetasy.2008.07.012

  日期：2008.7

  Biocatalytic deracemisation of racemic allylic alcohols by whole cells of Candida parapsilosis ATCC 7330 resulted in the formation of the (R)-enantiomers in high enantiomeric excesses (up to >99%) and isolated yields (up to 79%). (C) 2008 Elsevier Ltd. All rights reserved.
• Enantioselective reduction of α,β-enones using an oxazaborolidine catalyst generated in situ from a chiral lactam alcohol
  作者：Yasuhiro Kawanami、Yudai Mikami、Kazuya Kiguchi、Yuki Harauchi、Ryo C. Yanagita

  DOI：10.1016/j.tetasy.2011.10.018

  日期：2011.11

  The oxazaborolidine catalyst prepared in situ from the chiral lactam alcohol 3 and 4-iodophenoxyborane was found to catalyze the enantioselective reduction of α,β-enones at −40 °C with a high level of enantioselectivity of up to 90% ee.

  发现由手性内酰胺醇3和4-碘苯氧基硼烷原位制备的恶唑硼烷催化剂在-40℃下以高达90％ee的高对映选择性催化α，β-烯酮的对映选择性还原。