α-(cyclohex-1-enyl)-γ-butyrolactone | 32591-07-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: α-(cyclohex-1-enyl)-γ-butyrolactone
• 英文别名: 3-(cyclohex-1-en-1-yl)dihydrofuran-2(3H)-one；2-Cyclohex-1-enylbutyrolacton；3-cyclohex-1-enyl-dihydro-furan-2-one；3-(cyclohexen-1-yl)oxolan-2-one
• CAS: 32591-07-4
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: FWWFHEVCXWZEFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  α-(cyclohex-1-enyl)-γ-butyrolactone 在 sodium hydroxide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.75h， 生成 spiro-3-carboxylic acid, methyl ester
  参考文献：
  名称：

  Stereochemical control in cyclofunctionalization of olefinic alcohols and olefinic phenols with benzeneselenenyl chloride

  摘要：

  DOI：

  10.1021/jo00187a031
• 作为产物：
  描述：

  α-cyclohexylidene-γ-butyrolactone 以 甲醇 为溶剂， 反应 6.5h， 以77%的产率得到α-(cyclohex-1-enyl)-γ-butyrolactone
  参考文献：
  名称：

  A Convenient Synthesis of α-Vinyl-lactones by Photo-Deconjugation of α,β-Unsaturated γ- or δ-Lactones

  摘要：

  DOI：

  10.1055/s-1983-30609

文献信息

• Ni-catalyzed cross-electrophile coupling of α-hydroxy carbonyl compound-derived oxalates with vinyl triflates
  作者：Xianghua Tao、Ken Yao、Weichao Xue

  DOI：10.1016/j.tetlet.2021.153129

  日期：2021.6

  A nickel-catalyzed reductive vinylation of α-hydroxy carbonyl compound-derived C–O electrophiles to access β,γ-unsaturated carbonyl compounds is reported here. By this method, a library of vinyl triflates can serve as vinylating reagents, while various alkyl oxalates undergo C–O bond fragmentation to provide α-carbonyl radicals. This work expands the scope of cross-electrophile coupling reactions that

  本文报道了镍催化的 α-羟基羰基化合物衍生的 C-O 亲电试剂的还原乙烯基化反应，以获取 β,γ-不饱和羰基化合物。通过这种方法，乙烯基三氟甲磺酸酯库可以作为乙烯基化试剂，而各种草酸烷基酯进行 C-O 键断裂以提供 α-羰基自由基。这项工作扩展了交叉亲电偶联反应的范围，该反应采用两种低毒的 C-O 亲电试剂作为偶联伙伴。
• Domino Strategy for the Stereoselective Construction of Angularly Fused Tricyclic Ethers
  作者：B. V. Subba Reddy、Durgaprasad Medaboina、S. Gopal Reddy、V. Hanuman Reddy、Kiran Kumar Singarapu、Balasubramanian Sridhar

  DOI：10.1021/acs.joc.5b02241

  日期：2015.12.18

  A stereoselective synthesis of decahydrofuro [3,2-d]-isochromene derivatives has been achieved by the condensation of cyclohexenylbutane-1,4-diol with aldehydes in the presence of a stochiometric amount of BF3 center dot OEt2 in dichloromethane at -78 degrees C. Similarly, the condensation of 2-cyclopentenylbutan-1,4-diol with aldehydes provides the corresponding octahydro-2H-cyclopenta[c]furo-[2,3-d]pyran derivatives in good yields with high diastereoseleetivity. It is an,elegant strategy for the quick construction of tricyclic architectures with four contiguous stereogenic centers in a single step. These tricyclic frameworks are the integral part of numerous natural products.
• HENIN, F.;MORTEZAEI, R.;PETE, J. -P., SYNTHESIS, BRD, 1983, N 12, 1019-1021
  作者：HENIN, F.、MORTEZAEI, R.、PETE, J. -P.

  DOI：——

  日期：——
• SCHULTZ, A. G.;SUNDARARAMAN, PADMANABHAN, J. ORG. CHEM., 1984, 49, N 13, 2455-2462
  作者：SCHULTZ, A. G.、SUNDARARAMAN, PADMANABHAN

  DOI：——

  日期：——
• MORTEZAEI, REZA;PIVA, OLIVIER;HENIN, FRANCOISE;MUZART, JACQUES;PETE, JEAN+, TETRAHEDRON LETT., 27,(1986) N 26, 2997-3000
  作者：MORTEZAEI, REZA、PIVA, OLIVIER、HENIN, FRANCOISE、MUZART, JACQUES、PETE, JEAN+

  DOI：——

  日期：——