3-methylbut-2-en-1-yl phenyl carbonate | 138621-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methylbut-2-en-1-yl phenyl carbonate
• 英文别名: 3-Methylbut-2-enyl phenyl carbonate
• CAS: 138621-74-6
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: GFWSUTMWGMNRLX-UHFFFAOYSA-N

物化性质

• 沸点：
  289.0±23.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methylbut-2-en-1-yl phenyl carbonate 在 palladium diacetate 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以42%的产率得到((2-methylbut-3-en-2-yl)oxy)benzene
  参考文献：
  名称：

  Synthesis of allylic aryl ethers via palladium-catalyzed decarboxylation of allylic aryl carbonates

  摘要：

  Allylic aryl ethers are readily prepared in high yield by the palladium-catalyzed decarboxylation of allylic aryl carbonates.

  DOI：

  10.1016/0040-4039(91)80156-z
• 作为产物：
  描述：

  氯甲酸苯酯 、 异戊烯醇 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以33%的产率得到3-methylbut-2-en-1-yl phenyl carbonate
  参考文献：
  名称：

  亲核 Fe 催化中的氧化还原活性三唑鎓衍生配体 - 反应性分布和区域选择性 O-烯丙基化的发展

  摘要：

  三唑鎓衍生的 N-杂环卡宾 (aNHC) 配体通过相应三唑鎓盐的去质子化很容易获得，被证明是各种烯丙基取代反应中的通用配体。相应的三唑鎓盐是由叠氮化物和炔烃通过 1,3-偶极环加成和 N-烷基化反应形成的。这些配体的独特性质是在其释放形式时是两性离子的，并作为强氧化还原活性 σ-供体配体。凭借这些特性，这些配体能够开发出前所未有的 Fe 催化的烯丙基碳酸酯区域选择性芳氧基化。

  DOI：

  10.1002/ejoc.201300902

文献信息

• Nickel-Catalyzed Reductive Allylation of Tertiary Alkyl Halides with Allylic Carbonates
  作者：Haifeng Chen、Xiao Jia、Yingying Yu、Qun Qian、Hegui Gong

  DOI：10.1002/anie.201705521

  日期：2017.10.9

  of all C(sp3) quaternary centers has been successfully achieved under Ni‐catalyzed cross‐electrophile coupling of allylic carbonates with unactivated tertiary alkyl halides. For allylic carbonates bearing C1 or C3 substituents, the reaction affords excellent regioselectivity through the addition of alkyl groups to the unsubstituted allylic carbon terminus. The allylic alkylation method also exhibits

  在烯丙基碳酸酯与未活化叔烷基卤化物的镍催化交叉亲电子偶联下，已成功实现了所有C（sp 3）季铵盐中心的构建。对于带有C1或C3取代基的烯丙基碳酸酯，该反应通过向未取代的烯丙基碳末端加成烷基而提供了优异的区域选择性。烯丙基烷基化方法还具有出色的官能团相容性，并提供具有高E 选择性的产品。
• Redox-Active Triazolium-Derived Ligands in Nucleophilic Fe-Catalysis - Reactivity Profile and Development of a Regioselective<i>O</i>-Allylation
  作者：Johannes E. M. N. Klein、Michael S. Holzwarth、Stephan Hohloch、Biprajit Sarkar、Bernd Plietker

  DOI：10.1002/ejoc.201300902

  日期：2013.10

  Triazolium-derived N-heterocyclic carbene (aNHC) ligands, which are readily accessible by deprotonation of the corresponding triazolium salts, proved to be versatile ligands in diverse allylic substitution reactions. The corresponding triazolium salts are formed from azides and alkynes through the application of 1,3-dipolar cycloaddition and N-alkylation reactions. The unique property of these ligands

  三唑鎓衍生的 N-杂环卡宾 (aNHC) 配体通过相应三唑鎓盐的去质子化很容易获得，被证明是各种烯丙基取代反应中的通用配体。相应的三唑鎓盐是由叠氮化物和炔烃通过 1,3-偶极环加成和 N-烷基化反应形成的。这些配体的独特性质是在其释放形式时是两性离子的，并作为强氧化还原活性 σ-供体配体。凭借这些特性，这些配体能够开发出前所未有的 Fe 催化的烯丙基碳酸酯区域选择性芳氧基化。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE CYCLOPROPANE COMPOUND AND ASYMMETRIC COPPER COMPLEX FOR USE IN THE SAME
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1674445A1

  公开（公告）日：2006-06-28

  A process for producing an optically active cyclopropane compound represented by the formula (4): wherein R3, R4, R5 and R6 are the same or different, and represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, and so on; and R7 represents a C1-6 alkyl group; and * represents an asymmetric carbon atom, which comprises reacting a prochiral olefin represented by the formula (2): wherein R3, R4, R5, and R6 are as described above, with a diazoacetic acid ester represented by the formula (3):         N2CHCO2R7     (3) wherein R7 is as defined above, in the presence of an asymmetric copper complex prepared from an optically active cycloalkylidenebisoxazoline compound represented by the formula (1): wherein R1 represents a hydrogen atom, a C1-6 alkyl group, and so on; R2 represents a C1-6 alkyl group and so on; and n represents an integer of 0 to 3; provided that, two R1s may be bonded each other together with the carbon atom to which they are bonded to form a ring; and * represents an asymmetric carbon atom, and a copper compound, is provided.

  一种生产由式（4）表示的光学活性环丙烷化合物的工艺： 其中 R3、R4、R5 和 R6 相同或不同，代表氢原子、卤素原子、取代或未取代的烷基等；R7 代表 C1-6 烷基；* 代表不对称碳原子、 其中包括使式 (2) 所代表的手性烯烃发生反应： 其中 R3、R4、R5 和 R6 如上所述，与式 (3) 所代表的重氮乙酸酯反应： N2CHCO2R7 (3) 其中 R7 如上定义，在由式（1）代表的光学活性环烷基亚双噁唑啉化合物制备的不对称铜络合物存在下： 其中，R1 代表氢原子、C1-6 烷基等；R2 代表 C1-6 烷基等；n 代表 0 至 3 的整数；条件是两个 R1 可与它们所键合的碳原子一起相互键合以形成环；* 代表不对称碳原子、 以及一种铜化合物。
• METHOD FOR PRODUCING OPTICALLY ACTIVE CYCLOPROPANECARBOXYLATE COMPOUND
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1783111B1

  公开（公告）日：2015-04-08
• Process for producing optically active cyclopropane compound and asymmetric copper complex for use in the same
  申请人：Itagaki Makoto

  公开号：US20070032659A1

  公开（公告）日：2007-02-08

  A process for producing an optically active cyclopropane compound represented by the formula (4): wherein R 3 , R 4 , R 5 and R 6 are the same or different, and represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, and so on; and R 7 represents a C1-6 alkyl group; and * represents an asymmetric carbon atom, which comprises reacting a prochiral olefin represented by the formula (2): wherein R 3 , R 4 , R 5 , and R 6 are as described above, with a diazoacetic acid ester represented by the formula (3): N 2 CHCO 2 R 7 (3) wherein R 7 is as defined above, in the presence of an asymmetric copper complex prepared from an optically active cycloalkylidenebisoxazoline compound represented by the formula (1): wherein R 1 represents a hydrogen atom, a C1-6 alkyl group, and so on; R 2 represents a C1-6 alkyl group and so on; and n represents an integer of 0 to 3; provided that, two R 1 s may be bonded each other together with the carbon atom to which they are bonded to form a ring; and * represents an asymmetric carbon atom, and a copper compound, is provided.