3-(allyloxy)-3-(prop-2-ynyl)cyclohex-1-ene | 1609242-79-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(allyloxy)-3-(prop-2-ynyl)cyclohex-1-ene
• 英文别名: 3-Prop-2-enoxy-3-prop-2-ynylcyclohexene；3-prop-2-enoxy-3-prop-2-ynylcyclohexene
• CAS: 1609242-79-6
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: BWCCDFRLPDFTBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  dicobalt octacarbonyl 、 3-(allyloxy)-3-(prop-2-ynyl)cyclohex-1-ene 在 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 以85%的产率得到7',7a'-dihydro-1'H-spiro[cyclohex[2]ene-1,3'-cyclopenta[c]pyran]-6'(4'H)-one
  参考文献：
  名称：

  Chemoenzymatic route to various spirocyclic compounds based on enantiomerically enriched tertiary allylic, homoallylic, and homopropargylic alcohols

  摘要：

  A ring closing metathesis (RCM) reaction of dienes and an intramolecular Pauson-Khand (PKR) reaction of enynes derived from tertiary allyl, homoallyl, and homopropargyl alcohol backbones to afford the corresponding spirocyclic dihydrofuran and dihydropyrans and spirocyclic cyclopentenone pyrans, respectively, are described. Cyclopent-2-ene anchored tertiary allyl, homoallyl, and homopropargyl alcohols la-c have been efficiently resolved via enzymatic resolution with high ee (up to 90%) with 44%, 40%, and 43% chemical yields, respectively. Moreover, the cyclohex-2-ene anchored tertiary allyl, homoallyl, and homopropargyl alcohols 3a-c have also been resolved in the same manner with high ee (up to 97%) and in 42%, 45%, and 49% chemical yields. Enantiomerically enriched dienes derived from tertiary homoallyl alcohols yield the corresponding enantiomerically enriched spirocyclic dihydropyran derivatives via RCM with 74% and 78% chemical yields and with 90% and 97% ee, respectively. Moreover, enantiomerically enriched enynes derived from tertiary homoallyl alcohols afford the corresponding enantiomerically enriched cyclopentenone pyrans with spirocyclic motifs via PKR with 80% and 81% chemical yields, respectively, and as single diastereomers. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.03.004
• 作为产物：
  描述：

  2-环己烯-1-酮 在 锌铜偶 、 potassium hydride 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 7.83h， 生成 3-(allyloxy)-3-(prop-2-ynyl)cyclohex-1-ene
  参考文献：
  名称：

  生物催化光学活性叔醇

  摘要：

  摘要 最初，化学酶法制备光学活性芳香环稠环叔醇 (S)-(–)-1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol-(–)-1b, (S) -(+)-1-methyl-2,3-dihydro-1H-inden-1-ol-(+)-1a 已有报道。[9] CAL-A（来自南极念珠菌的脂肪酶-A）被发现是 1b 的最佳生物催化剂，CAL-A 交联酶聚集体 (CLEA) 是 1a 的 ee 值为 20% 和 45%，酯 2b 和 2a 的 ee 值为 99和 71%。然后，环戊二烯锚定的叔烯丙基 1a'、高烯丙基 1b' 和高炔丙基 1c 醇以高 ee（高达 90%）进行酶促拆分，化学收率分别为 44%、40% 和 43%，环己基 2 -ene 在高 ee（高达 97%）中锚定叔烯丙基 3a、高烯丙基 3b 和高炔丙基 3c 醇，化学产率依次为 42%、45% 和

  DOI：

  10.1080/00397911.2016.1274032

文献信息

• Chemoenzymatic route to various spirocyclic compounds based on enantiomerically enriched tertiary allylic, homoallylic, and homopropargylic alcohols
  作者：Cihangir Tanyeli、Devrim Özdemirhan

  DOI：10.1016/j.tetasy.2014.03.004

  日期：2014.4

  A ring closing metathesis (RCM) reaction of dienes and an intramolecular Pauson-Khand (PKR) reaction of enynes derived from tertiary allyl, homoallyl, and homopropargyl alcohol backbones to afford the corresponding spirocyclic dihydrofuran and dihydropyrans and spirocyclic cyclopentenone pyrans, respectively, are described. Cyclopent-2-ene anchored tertiary allyl, homoallyl, and homopropargyl alcohols la-c have been efficiently resolved via enzymatic resolution with high ee (up to 90%) with 44%, 40%, and 43% chemical yields, respectively. Moreover, the cyclohex-2-ene anchored tertiary allyl, homoallyl, and homopropargyl alcohols 3a-c have also been resolved in the same manner with high ee (up to 97%) and in 42%, 45%, and 49% chemical yields. Enantiomerically enriched dienes derived from tertiary homoallyl alcohols yield the corresponding enantiomerically enriched spirocyclic dihydropyran derivatives via RCM with 74% and 78% chemical yields and with 90% and 97% ee, respectively. Moreover, enantiomerically enriched enynes derived from tertiary homoallyl alcohols afford the corresponding enantiomerically enriched cyclopentenone pyrans with spirocyclic motifs via PKR with 80% and 81% chemical yields, respectively, and as single diastereomers. (C) 2014 Elsevier Ltd. All rights reserved.
• Optically active tertiary alcohols by biocatalysis
  作者：Devrim Özdemirhan

  DOI：10.1080/00397911.2016.1274032

  日期：2017.4.3

  chemoenzymatic route to optically active aromatic ring-fused cyclic tertiary alcohols (S)-(–)-1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol-(–)-1b, (S)-(+)-1-methyl-2,3-dihydro-1H-inden-1-ol-(+)-1a has been reported.[9] CAL-A (lipase-A from Candida antarctica) was found the best biocatalyst for 1b, CAL-A cross linked enzyme aggregate (CLEA) for 1a, with ee values of 20 and 45% and the esters 2b and 2a with ee values

  摘要 最初，化学酶法制备光学活性芳香环稠环叔醇 (S)-(–)-1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol-(–)-1b, (S) -(+)-1-methyl-2,3-dihydro-1H-inden-1-ol-(+)-1a 已有报道。[9] CAL-A（来自南极念珠菌的脂肪酶-A）被发现是 1b 的最佳生物催化剂，CAL-A 交联酶聚集体 (CLEA) 是 1a 的 ee 值为 20% 和 45%，酯 2b 和 2a 的 ee 值为 99和 71%。然后，环戊二烯锚定的叔烯丙基 1a'、高烯丙基 1b' 和高炔丙基 1c 醇以高 ee（高达 90%）进行酶促拆分，化学收率分别为 44%、40% 和 43%，环己基 2 -ene 在高 ee（高达 97%）中锚定叔烯丙基 3a、高烯丙基 3b 和高炔丙基 3c 醇，化学产率依次为 42%、45% 和