hepta-1,6-dien-4-yl benzoate

• 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: hepta-1,6-dien-4-yl benzoate
• 英文别名: 1,6-heptadiene-4-yl benzoate
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: UHVGTWZWBZIKGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  hepta-1,6-dien-4-yl benzoate 在 二(3-甲基丁烷-2-基)硼烷 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 生成 庚烷-1,4,7-三醇
  参考文献：
  名称：

  Synthesis of Glycerol Homologues

  摘要：

  A series of monoprotected glycerol homologues and triols were prepared in high overall yields (>90%) via the hydroboration-oxidation of the corresponding dienols. Hydroboration with disiamylborane and concomitant alkaline oxidation (NaOH, H2O2) was found to be a mild, high-yielding, and highly efficient method for the construction of a variety of glycerol homologues.

  DOI：

  10.1055/s-0033-1339185
• 作为产物：
  描述：

  1,6-庚二烯-4-醇 、 氯化苄 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以92%的产率得到hepta-1,6-dien-4-yl benzoate
  参考文献：
  名称：

  Synthesis of Glycerol Homologues

  摘要：

  A series of monoprotected glycerol homologues and triols were prepared in high overall yields (>90%) via the hydroboration-oxidation of the corresponding dienols. Hydroboration with disiamylborane and concomitant alkaline oxidation (NaOH, H2O2) was found to be a mild, high-yielding, and highly efficient method for the construction of a variety of glycerol homologues.

  DOI：

  10.1055/s-0033-1339185

文献信息

• Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts
  作者：Shota Nagasawa、Yusuke Sasano、Yoshiharu Iwabuchi

  DOI：10.1002/anie.201607752

  日期：2016.10.10

  Few methods allow for the direct conversion of cycloalkenes into cycloalkadienes with high chemo‐ and regioselectivity. Herein, we report a convenient one‐pot process for this transformation that involves the unprecedented N‐preferential group transfer of N‐oxoammonium salts to cycloalkenes, followed by Cope elimination, to afford cycloalkadienes at room temperature and pressure.

  很少有方法能够将环烯烃直接转化为具有高化学和区域选择性的环烷二烯。在此，我们提出一个方便的一锅法用于该转化，其涉及的前所未有的N-优先基团转移Ñ -oxoammonium盐环烯烃，随后柯普消除，以得到在室温和压力环二烯。
• Synthesis of Symmetrical Trisubstituted Olefins by Cross Metathesis
  作者：Arnab K. Chatterjee、Daniel P. Sanders、Robert H. Grubbs

  DOI：10.1021/ol0259793

  日期：2002.5.1

  [reaction: see text] Trisubstituted alkenes have been prepared via intermolecular olefin cross-metathesis (CM) between alpha-olefins and symmetrically 1,1-disubstituted olefins using an imidazolylidene ruthenium benzylidene complex. Of particular interest is the synthesis of isoprenoid/prenyl groups by a simple solvent-free CM reaction with isobutylene. In addition, prenyl groups can also be installed

  [反应：见正文]使用咪唑基亚甲基钌亚苄基络合物，通过α-烯烃与对称的1,1-二取代烯烃之间的分子间烯烃交叉复分解（CM）制备了三取代烯烃。特别令人感兴趣的是通过与异丁烯的简单无溶剂CM反应合成类异戊二烯/异戊二烯基。另外，异戊二烯基还可以通过2-甲基-2-丁烯与各种α-烯烃在室温下以低催化剂负载量的交叉复分解来安装。
• Ruthenium metathesis catalyst and method for producing olefin reaction product by metathesis reaction using the same
  申请人：Takasago International Corporation

  公开号：US06313365B1

  公开（公告）日：2001-11-06

  The invention has an object of safely and simply preparing a large amount of a ruthenium metathesis catalyst, which is used as a catalyst for a carbon-carbon bond formation using, particularly, a metathesis reaction. The metathesis catalyst has the following complex composition (A) or (B). The composition (A) includes RuX12(arene)(PR1R2R3) and R4CHX22, R5C ≡CH or R4CHX2 and a reducing agent, wherein X1 and X2 respectively are a halogen atom; arene is a hydrocarbon having a benzene ring; R1, R2 and R3, which may be the same or different, respectively are an alkyl group having 1-8 carbon atoms, a cycloalkyl group having 3-8 carbon atoms or an optionally substituted aryl group, wherein the substituent group is an alkyl group having 1-8 carbon atoms, an alkoxy group having 1-8 carbon atoms, an alkylamino group having 1-8 carbon atoms or a halogen atom; R4 is an alkyl group which has 1-8 carbon atoms and may have an ether bond or an ester bond, an optionally subsituted aryl group, wherein the substituent group is a halogen atom or a hydroxyl group; or cycloalkyl group having 3-8 carbon atoms; and R5 is an optionally substituted alkyl group which has 1-8 carbon atoms and may have an ether bond or an ester bond, wherein the substituent group is a halogen atom or a hydroxyl group, an aryl group or a cycloalkyl group having 3-8 carbon atoms. The composition B includes [RuX12(arene)]2, PR1R2R3, R5C≡CH or R4CHX2 and a reducing agent, wherein X1, arene, R1, R2, R3, R4 and R5 are the same as defined above.

  该发明的目的是安全简便地制备大量的钌助剂，该助剂用于碳－碳键形成的催化剂，特别是用于交换反应。该交换催化剂具有以下复合组成（A）或（B）。组成（A）包括RuX12（芳烃）（PR1R2R3）和R4CHX22，R5C≡CH或R4CHX2和还原剂，其中X1和X2分别是卤素原子；芳烃是具有苯环的碳氢化合物；R1、R2和R3分别是具有1-8个碳原子的烷基，具有3-8个碳原子的环烷基或者是可选取代的芳基，其中取代基是具有1-8个碳原子的烷基，具有1-8个碳原子的烷氧基，具有1-8个碳原子的烷基氨基或卤素原子；R4是具有1-8个碳原子的烷基，可能具有醚键或酯键，可选取代的芳基，其中取代基是卤素原子或羟基；或者是具有3-8个碳原子的环烷基；R5是可选取代的具有1-8个碳原子的烷基，可能具有醚键或酯键，其中取代基是卤素原子或羟基，芳基或具有3-8个碳原子的环烷基。组成（B）包括[RuX12（芳烃）]2，PR1R2R3，R5C≡CH或R4CHX2和还原剂，其中X1、芳烃、R1、R2、R3、R4和R5与上述定义相同。
• Cross-metathesis reaction of functionalized and substituted olefins using group 8 transition metal carbene complexes as metathesis catalysts
  申请人：Grubbs H. Robert

  公开号：US20070155975A1

  公开（公告）日：2007-07-05

  The invention pertains to the use of Group 8 transition metal carbene complexes as catalysts for olefin cross-metathesis reactions. In particular, ruthenium and osmium alkylidene complexes substituted with an N-heterocyclic carbene ligand are used to catalyze cross-metathesis reactions to provide a variety of substituted and functionalized olefins, including phosphonate-substituted olefins, directly halogenated olefins, 1,1,2-trisubstituted olefins, and quaternary allylic olefins. The invention further provides a method for creating functional diversity using the aforementioned complexes to catalyze cross-metathesis reactions of a first olefinic reactant, which may or may not be substituted with a functional group, with each of a plurality of different olefinic reactants, which may or may not be substituted with functional groups, to give a plurality of structurally distinct olefinic products. The methodology of the invention is also useful in facilitating the stereoselective synthesis of 1,2-disubstituted olefins in the cis configuration.
• CROSS-METATHESIS REACTION OF FUNCTIONALIZED AND SUBSTITUTED OLEFINS USING GROUP 8 TRANSITION METAL CARBENE COMPLEXES AS METATHESIS CATALYSTS
  申请人：California Institute Of Technology

  公开号：US20140288319A1

  公开（公告）日：2014-09-25

  The invention pertains to the use of Group 8 transition metal carbene complexes as catalysts for olefin cross-metathesis reactions. In particular, ruthenium and osmium alkylidene complexes substituted with an N-heterocyclic carbene ligand are used to catalyze cross-metathesis reactions to provide a variety of substituted and functionalized olefins, including phosphonate-substituted olefins, directly halogenated olefins, 1,1,2-trisubstituted olefins, and quaternary allylic olefins. The invention further provides a method for creating functional diversity using the aforementioned complexes to catalyze cross-metathesis reactions of a first olefinic reactant, which may or may not be substituted with a functional group, with each of a plurality of different olefinic reactants, which may or may not be substituted with functional groups, to give a plurality of structurally distinct olefinic products. The methodology of the invention is also useful in facilitating the stereoselective synthesis of 1,2-disubstituted olefins in the cis configuration.