n-butyl cyanoformate | 5532-84-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: n-butyl cyanoformate
• 英文别名: butyl cyanoformate；Cyanoameisensaeure-n-butylester
• CAS: 5532-84-3
• 化学式: C₆H₉NO₂
• 分子量: 127.143
• InChiKey: IDRIISKVLZHPDP-UHFFFAOYSA-N

物化性质

• 沸点：
  159-160 °C
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  n-butyl cyanoformate 以85%的产率得到5-butoxycarbonylthieno[2,3-c]pyridine
  参考文献：
  名称：

  THIENOPYRIDINE DERIVATIVE, METHOD FOR PRODUCING SAME AND ORGANIC SEMICONDUCTOR DEVICE USING SAME

  摘要：

  本发明涉及一种新颖的噻吩并吡啶衍生物，其化学式表示为（1），该衍生物可用作有机半导体器件，如有机薄膜晶体管元件，本发明还涉及制备化学式（1）所表示的噻吩并吡啶衍生物的方法：

  公开号：

  US20130005979A1
• 作为产物：
  描述：

  氰化钾 、 氯甲酸丁酯 在 18-冠醚-6 作用下， 以 二氯甲烷 为溶剂， 生成 n-butyl cyanoformate
  参考文献：
  名称：

  Preparation of cyanoformates. Crown ether phase transfer catalysis

  摘要：

  DOI：

  10.1021/jo00883a041

文献信息

• Cyanoesterification of norbornenes catalyzed by palladium: facile synthetic methodology to introduce cyano and ester functionalities via direct carbon–carbon bond cleavage of cyanoformates
  作者：Yasushi Nishihara、Yoshiaki Inoue、Seisuke Izawa、Mitsuru Miyasaka、Kenki Tanemura、Kiyohiko Nakajima、Kentaro Takagi

  DOI：10.1016/j.tet.2006.08.025

  日期：2006.10

  Addition of cyanoformates (NC–COOR) to norbornene at 110 °C in the presence of Pd(PPh3)4 (10 mol %) as a catalyst affords with high selectivity the corresponding doubly functionalized polar norbornane derivatives bearing both cyano and ester groups. By using benzonorbornadiene and norbornadienes as the substrates, the reaction can be extended to synthesis of various functionalized norbornene derivatives

  在Pd（PPh 3）4（10 mol％）作为催化剂的存在下，在110°C的氰基甲酸酯（NC-COOR）加至降冰片烯中，可同时具有氰基和酯基的双官能极性降冰片烷衍生物相应地具有较高的选择性。通过使用苯并降冰片二烯和降冰片二烯作为底物，反应可以扩展到合成各种官能化的降冰片烯衍生物，产率中等至优异。在大多数情况下烷基，如甲基，乙基，Ñ丙基，异丙丙基，Ñ丁基，叔酯官能团中的-丁基和苄基适用于该反应。氰基甲酸酯向Pd（0）的氧化加成，降冰片烯的插入以及相应加合物的还原消除构成了拟议的催化途径。
• Intermediates for producing pyridine derivatives
  申请人：Kuraray Co., Ltd.

  公开号：US06111111A1

  公开（公告）日：2000-08-29

  A pyridine alcohol derivative represented by General Formula III ##STR1## (where A represents a divalent organic group which may contain one to three oxygen atoms, nitrogen atoms and/or sulfur atoms, wherein A may form a 5-, 6-, 7-, or 8-membered ring together with two bonded carbon atoms, where said ring may form a condensed ring with one or more additional rings; R.sup.5 represents a hydrogen atom, --CHR.sup.1 R.sup.2, or an alkenyl group, an aryl group or an aralkyl group which may be substituted; R.sup.1 and R.sup.2 each independently represent a hydrogen atom or a hydrocarbon group which may be substituted; and R.sup.6 represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group or an aralkyl group which may be substituted), is produced by: reacting a pyridine ester derivative represented by General Formula I-1 ##STR2## (where Z.sup.1 represents --COX; X represents an alkoxyl group, an alkenyloxy group, an aryloxy group or an aralkyloxy group which may be substituted; and A is the same as above) with a reducing agent, an alkylating agent, an alkenylating agent, an arylating agent or an aralkylating agent to obtain a pyridine carbonyl derivative represented by General Formula II ##STR3## (where A and R.sup.5 are the same as above); and reacting the resulting pyridine carbonyl derivative with a reducing agent, an alkylating agent, an alkenylating agent, an arylating agent or an aralkylating agent to obtain the pyridine alcohol derivative of the General Formula III.

  通用公式III所代表的吡啶醇衍生物是通过以下步骤制备的：将通用公式I-1所代表的吡啶酯衍生物与还原剂、烷基化剂、烯基化剂、芳基化剂或芳基烷基化剂反应，得到通用公式II所代表的吡啶羰基衍生物；然后将所得的吡啶羰基衍生物与还原剂、烷基化剂、烯基化剂、芳基化剂或芳基烷基化剂反应，得到通用公式III所示的吡啶醇衍生物。
• Preparation, Structures, and Thermal Reactivity of Alkoxycarbonyl(cyano)palladium(II) Complexes <i>trans</i>-Pd(COOR)(CN)(PPh₃)₂ (R = Me, Et, <i>ⁿ</i>Pr, <i>ⁱ</i>Pr, <i>ⁿ</i>Bu, <i>^t</i>Bu, and Bn) as Intermediates of the Palladium-Catalyzed Cyanoesterification of Norbornene Derivatives
  作者：Yasushi Nishihara、Mitsuru Miyasaka、Yoshiaki Inoue、Tomoka Yamaguchi、Masaaki Kojima、Kentaro Takagi

  DOI：10.1021/om700343y

  日期：2007.7.30

  complexes trans-Pd(COOR)(CN)(PPh3)2 (1, R = Me; 2, R = Et; 3, R = nPr; 4, R = iPr; 5, R = nBu; 6, R = tBu; 7, R = Bn) are prepared via oxidative addition of the corresponding cyanoformates to Pd(PPh3)4 in toluene at room temperature or 50 °C and characterized by means of NMR (1H, 13C1H}, and 31P1H}) and IR spectroscopy as well as elemental analyses. X-ray crystallography of 3, 4, and 6 showed a square-planar

  烷氧羰基（氰基）钯（II）配合物反式-Pd（COOR）（CN）（PPh 3）2（1，R = Me; 2，R = Et; 3，R = n; 4，R = i; 5，R = n卜; 6，R =吨卜; 如图7所示，R = Bn）是通过在室温或50°C下于甲苯中将相应的氰基甲酸酯氧化添加到Pd（PPh 3）4中制备的，并通过NMR（1 H，13 C 1 H}和31 P 1 H}）和IR光谱以及元素分析。的X射线晶体3，4，和6显示周围被结合到烷氧基羰基和氰基配体在所述的Pd中心的正方形平面协调反式构型。将Pd-CN和Pd-COOR债券1，3，4，和6与迄今报道的氰基钯（II）和烷氧基羰基钯（II）配合物的那些相似。在Pd（PPh 3）4与氰基甲酸苯酯反应后，发生热诱导的配体交换，从而生成双氰基钯（II）配合物，即反式-Pd（CN）2（PPh 3）2（8）。配合物2能够催化降冰片二烯与氰基甲酸乙酯反应生成（2
• Synthesis, Structure, and Isomerization of Alkoxycarbonyl(chloro)(cyano)rhodium(III) Complexes, <i>mer</i>-[RhCl(CO₂R)(CN)(PMe₃)₃] (R = Me, Et, <i>ⁿ</i>Pr, <i>ⁱ</i>Pr, <i>ⁿ</i>Bu, and Bn), through C–C Bond Cleavage of Cyanoformates
  作者：Yasuhiro Okuda、Takeru Okamoto、Arisa Yamamoto、Jing Li、Kiyohiko Nakajima、Yasushi Nishihara

  DOI：10.1246/cl.131072

  日期：2014.4.5

  Alkoxycarbonyl(chloro)(cyano)rhodium(III) complexes mer-[RhCl(CO2R)(CN)(PMe3)3] (1: R = Me; 2: R = Et; 3: R = nPr; 4: R = iPr; 5: R = nBu; 6: R = Bn) are prepared via oxidative addition of the corresponding cyanoformates to [RhCl(PMe3)3], derived in situ from [RhCl(cod)]2 and three equivalents of PMe3 in toluene at 70 °C, and their structures are characterized using NMR (1H, 13C1H}, and 31P1H}) and X-ray diffraction.

  烷氧基碳酰基（氯）（氰）铑（III）配合物 mer-[RhCl(CO2R)(CN)(PMe3)3]（1: R = Me; 2: R = Et; 3: R = nPr; 4: R = iPr; 5: R = nBu; 6: R = Bn）通过将相应的氰基甲酸酯氧化加成到 [RhCl(PMe3)3] 制备而成，后者是在70 °C下由 [RhCl(cod)]2 和三等摩尔的 PMe3 在甲苯中原位生成的，并通过 NMR（1H, 13C1H}, 和 31P1H}）及 X 射线衍射对其结构进行了表征。
• Method for producing pyridine derivatives
  申请人：Kuraray Co., Ltd.

  公开号：US06342606B2

  公开（公告）日：2002-01-29

  A pyridine alcohol derivative represented by General Formula III (where A represents a divalent organic group which may contain one to three oxygen atoms, nitrogen atoms and/or sulfur atoms, wherein A may form a 5-, 6-, 7-, or 8-membered ring together with two bonded carbon atoms, where said ring may form a condensed ring with one or more additional rings; R6 represents a hydrogen atom, —CHR1R2, or an alkenyl group, an aryl group or an aralkyl group which may be substituted; R1 and R2 each independently represent a hydrogen atom or a hydrocarbon group which may be substituted; and R represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group or an aralkyl group which may be substituted), is produced by: reacting a pyridine ester derivative represented by General Formula I-1

  一种由通式III表示的吡啶醇衍生物（其中A代表一个二价有机基团，可能含有一到三个氧原子、氮原子和/或硫原子，其中A可以与两个键合的碳原子一起形成一个5、6、7或8元环，该环可以与一个或多个额外的环形成一个紧凑环；R6代表氢原子，-CHR1R2，或烯基基团，芳基基团或芳基烷基基团，可以被取代；R1和R2分别独立地代表氢原子或可以被取代的碳氢基团；R代表氢原子，烷基基团，烯基基团，芳基基团或芳基烷基基团，可以被取代），通过以下方法制备：将由通式I-1表示的吡啶酯衍生物进行反应。