(R)-(-)-2-hydroxy-3E,5E-heptadienenitrile | 134929-89-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-(-)-2-hydroxy-3E,5E-heptadienenitrile
• 英文别名: (2R,3E,5E)-2-hydroxy-3,5-heptadienenitrile；(2R,3E,5E)-2-hydroxyhepta-3,5-dienenitrile
• CAS: 134929-89-8
• 化学式: C₇H₉NO
• 分子量: 123.155
• InChiKey: KKZBEJYQUGERIB-XOCXLOGJSA-N

物化性质

• 沸点：
  265.2±20.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  氯甲酸乙酯 、 (R)-(-)-2-hydroxy-3E,5E-heptadienenitrile 在 吡啶 作用下， 以89%的产率得到Carbonic acid (2E,4E)-(R)-1-cyano-hexa-2,4-dienyl ester ethyl ester
  参考文献：
  名称：

  在酶衍生的底物上通过金属催化的烯丙基取代合成E-乙烯基（R）-氨基酸衍生物

  摘要：

  氧合硝化酶衍生的烯丙基（R）-氰醇碳酸酯3和烯丙基（R）-α-羟基酯碳酸酯6被作为钯（0）催化的烯丙基叠氮化反应的底物进行了检测。研究了伴随的1，3-手性转位步骤的对映选择性和顺/反非对映选择性。发现氰基碳酸酯3a – c是令人印象深刻的底物，其产生的γ-叠氮基-α，β-不饱和腈4a – c具有接近1的顺式/反式比率，对映体过量范围为57％至85％。相反，碳酸酯6ab和b是反应的优异底物，仅提供相同对映体过量的95％ee的反式取代产物7a和b。

  DOI：

  10.1016/j.tetasy.2005.03.018
• 作为产物：
  描述：

  (E,E)-2,4-己二烯醛 、 丙酮氰醇 在 Prunus mume (R)-hydroxynitrile lyase 、 Na-citrate buffer 作用下， 以 异丙醚 为溶剂， 反应 56.0h， 以32%的产率得到(R)-(-)-2-hydroxy-3E,5E-heptadienenitrile
  参考文献：
  名称：

  PmHNL catalyzed synthesis of (R)-cyanohydrins derived from aliphatic aldehydes

  摘要：

  Hydroxynitrile lyase from the Japanese apricot (Prunus mume) catalyzes the formation of several aliphatic cyanohydrins in an asymmetric fashion. By employing a biphasic reaction system, aliphatic aldehydes with various structural features can be converted to the corresponding (R)-cyanohydrins with good overall yield and enantiomeric excess. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.003

文献信息

• A Facile Synthesis of Optically Active γ-Cyanoallylic Alcohols Using Asymmetric Hydrocyanation of α,β-Alkenyl Aldehydes Followed by Stereospecific [3.3]Sigmatropic Chirality Transfer of the Cyanohydrin Acetates
  作者：Hiroshi Abe、Hideaki Nitta、Atsunori Mori、Shohei Inoue

  DOI：10.1246/cl.1992.2443

  日期：1992.12

  Optically active γ-cyanoallylic alcohols were synthesized by using asymmetric hydrocyanation of α,β-alkenyl aldehydes catalyzed by peptide-titanium complex to give α-cyanoallylic alcohols (cyanohydrins) with high optical yields followed by palladium complex catalyzed [3.3]sigmatropic chirality transfer of the corresponding acetates.

  通过使用肽钛络合物催化α,β-烯基醛的不对称氰化反应，合成了光学活性的γ-氰基烯丙醇，得到高光学产率的α-氰基烯丙醇（氰基醇），随后通过钯络合物催化的相应乙酸酯的[3.3]σ迁移手性传递。
• Preparation of chiral cyanohydrins by an oxynitrilase-mediated transcyanation
  作者：Vassil I. Ognyanov、Violeta K. Datcheva、Keith S. Kyler

  DOI：10.1021/ja00018a042

  日期：1991.8

  The transcyanation of aromatic and aliphatic aldehydes 1 (RCHO) with acetone cyanohydrin is catalyzed by the enzyme D-oxynitrilase to afford (R)-cyanohydrins 2 (RCH(OH)CN). The biocatalytic method using acetone cyanohydrin gives products of high enantiomeric purity with better consistency than similar conditions using hydrogen cyanide as the cyanide source. The use of an ether-buffer biphasic solvent system is essential for producing products of optimum optical purity, but the solubility properties of the substrate have a pronounced effect on the enantiomeric purity of the final product. A discussion relating the solubility partition coefficient (log P) of a substrate to the enantiomeric purity of the product as a guide for predicting the outcome with new substrates is presented. Application of the method to the preparation of the following cyanohydrins is reported (R, ee): a, C6H5, 92% ee; b, 3,4-(CH2O2)C6H3, 90% ee; c, 2-(CH3O)C6H4, 96% ee; d, C6H5CH2, 88% ee; e, CH3SCH2CH2, 92% ee; f, CH3(CH2)5CH2, 92% ee; g, (CH3)3C, 92% ee; h, c-C6H11, 96% ee; i, CH3O2C(CH2)6CH2, 97% ee; j, (E,E)-CH3CH = CHCH = CH, 96% ee; k, (CH3)2C = CHCH2CH2C(CH3) = CH, 99% ee.
• Encapsulation of Biologicals within Silicate, Siloxane, and Hybrid Sol−Gel Polymers:  An Efficient and Generic Approach
  作者：Iqbal Gill、Antonio Ballesteros

  DOI：10.1021/ja9814568

  日期：1998.9.1

  The sol-gel encapsulation of labile biological materials with catalytic and recognition functions within robust polymer matrices remains a challenging task, despite the considerable research that has been focused on this field. Herein, we describe a new class of precursors, based around polyol silicates and polyol siloxanes, especially those derived from glycerol, that addresses problems faced with traditional bioencapsulation protocols. Poly(glyceryl silicate) (PGS) was prepared and employed for sol-gel bioentrapment, in an approach distinguished by a high biocompatibility and mild encapsulation conditions, and which enables the reproducible and efficient confinement of proteins and cells inside silica. The methodology was extended to metallosilicate, alkylsiloxane, functionalized siloxane, and composite sol-gels, thereby allowing the fabrication of a physicochemically diverse range of bio-doped polymers. The hybrid materials display activities approaching those of the free biologicals, together with the high stabilities and robustness that characterize sol-gel bioceramics. Indeed, the bioencapsulates performed better than those fabricated from tetramethoxysilane, poly (methyl silicate) or alcohol-free poly(silicic acid), even when the latter were doped with glycerol. The activity enhancements appear to derive at least in part from the unusual microstructure of PGS sol-gels, in particular their high porosity, although the underlying mechanisms are unclear. Differences in precursor hydrolysis/condensation, development of gel structure, biological-matrix interactions, precursor toxicity, and pore collapse probably all contribute to the observed efficiency of the PGS materials. The performances of the encapsulates are compared with conventional sol-biogels and other immobilizates, in representative biocatalyst, biosensor, and biodiagnostic applications.
• Study on the (R)-oxynitrilase activity of Pouteria sapota
  作者：Aida Solís、Héctor Luna、Norberto Manjarrez、Herminia I. Pérez

  DOI：10.1016/j.tet.2004.07.102

  日期：2004.11

  Mamey (Pouteria sapota) defatted meal was used to catalyze the enantioselective addition of HCN to alpha, beta-unsaturated aldehydes. Using a biphasic system of diisopropyl ether and citrate buffer (0.1 M, pH 5.0, 10% v/v), the (R)-cyanohydrins obtained showed good conversion (from 54 to 98%) and enantiomeric excess (from 74 to 99%). (C) 2004 Elsevier Ltd. All rights reserved.
• MATTHEWS, BARRY R.;JACKSON, W. ROY;JAYATILAKE, GAMINI S.;WILSHIRE, COLIN;+, AUSTRAL. J. CHEM., 41,(1988) N1, C. 1697-1709
  作者：MATTHEWS, BARRY R.、JACKSON, W. ROY、JAYATILAKE, GAMINI S.、WILSHIRE, COLIN、+

  DOI：——

  日期：——