2-(prop-2-yn-1-yl)cycloheptanone | 220043-96-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(prop-2-yn-1-yl)cycloheptanone
• 英文别名: 2-(prop-2-ynyl)cycloheptanone；2-propynylcyclopheptanone；Propargylcycloheptanone；2-prop-2-ynylcycloheptan-1-one
• CAS: 220043-96-9
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: MHDOXBYNUYJLMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(prop-2-yn-1-yl)cycloheptanone 在 mercuric triflate 作用下， 以 苯 为溶剂， 反应 4.0h， 以98%的产率得到2-methyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]furan
  参考文献：
  名称：

  Mercuric Triflate-Catalyzed Synthesis of 2-Methylfurans from 1-Alkyn-5-ones

  摘要：

  2-Methylfurans were prepared by an effective cyclization of 1-alkyn-5-ones in the presence of mercuric triflate as the catalyst under very mild reaction conditions with high catalytic turnover up to 100 times. Benzene, toluene, or dichloromethane was the solvent of choice.

  DOI：

  10.1021/ol048730p
• 作为产物：
  描述：

  cycloheptanone dimethylhydrazone 在 甲醇 、 正丁基锂 、 水 、 草酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 5.0h， 生成 2-(prop-2-yn-1-yl)cycloheptanone
  参考文献：
  名称：

  金催化的二炔基酯的1,3-乙酰氧基迁移/ 5-exo-dig环化/ 1,5-酰基迁移

  摘要：

  进行三班制：通过金催化的1,6-二炔基-3-基酯的重排，高收率立体选择性地形成了多共轭δ-二酮。这种级联反应涉及1,3-σ的酰氧基转移，所得烯丙炔的5- exo- dig环化反应以及酰基片段前所未有的1,5-σ的转移。有效的酸催化转化为复杂的多环骨架表明了产品的实用性。

  DOI：

  10.1002/anie.201101179

文献信息

• Synthesis of highly strained bicyclic[3.n.1]alkenes by a metal-catalyzed Conia-ene reaction
  作者：Shivakrishna Kallepu、Krishna Kumar Gollapelli、Jagadeesh Babu Nanubolu、Rambabu Chegondi

  DOI：10.1039/c5cc05926g

  日期：——

  A high yielding metal-catalysed Conia-ene reaction of 2-acetylenic ketones for the synthesis of bicyclo[3.n.1]alkenes has been developed.

  一种高产率的金属催化Conia-ene反应用于合成双环[3.n.1]烯烃的2-乙炔基酮已经被开发出来。
• Synergistic Catalysis: Metal/Proton-Catalyzed Cyclization of Alkynones Toward Bicyclo[3.<i>n</i>.1]alkanones
  作者：Shifa Zhu、Qiaohui Zhang、Kai Chen、Huanfeng Jiang

  DOI：10.1002/anie.201504964

  日期：2015.8.3

  highly efficient and practical synergistically metal/proton‐catalyzed Conia–ene reaction for the synthesis of bicyclo[3.n.1]alkanones has been developed. This synergistic catalysis was successfully utilized in modifying natural compounds such as methyl dihydrojasmonate, α,β‐thujone, and 5α‐cholestan‐3‐one. Furthermore, the bridged carbonyl group of bicyclo[3.2.1]alkanones could be easily attacked by nucleophiles

  已开发出一种高效且实用的协同金属/质子催化的Conia-ene反应合成双环[3.n.1]烷酮。这种协同催化作用已成功用于修饰天然化合物，例如二氢茉莉酮酸甲酯，α，β-thujone和5α-cholestan-3-one。此外，亲核试剂很容易攻击双环[3.2.1]链烷酮的桥连羰基，从而以优异的收率得到开环的环庚烯酮产物或双环[4.2.1]酰胺。这些反应提供了从简单的起始原料或天然存在的化合物快速进入各种环状结构的途径。
• Synthesis of functionalised furans and pyrroles through annulation reactions of 4-pentynones
  作者：Antonio Arcadi、Elisabetta Rossi

  DOI：10.1016/s0040-4020(98)00953-3

  日期：1998.12

  A new approach to 4-pentynones through palladium-catalysed coupling reaction of the ready available 2-propynyl ketones with aryl iodides and/or vinyl triflates is proposed. Annulation reactions of both 2-propynyl ketones and 4-pentynones gave functionalised furans using potassium tert-butoxide in DMF and functionalised pyrroles in the presence of benzylamine or ammonia, respectively in good to high

  提出了一种新的4-戊炔酮通过钯催化的2-丙炔基酮与芳基碘化物和/或乙烯基三氟甲磺酸酯的偶联反应的新方法。使用叔丁醇钾在DMF中的官能化呋喃和苄基胺或氨存在下的官能化吡咯分别进行2-丙炔基酮和4-戊炔酮的环化反应，收率良好或高收率。该方法已被扩展的17制备β -hydroxyandrost -4-烯并[3,2- b ] - （5-甲基）呋喃和17 β -hydroxyandrost -4-烯并[3,2- b]（1-苄基-5-甲基）吡咯。当将4-戊炔酮用甲醇钠的甲醇溶液处理时，观察到不同的反应模式。还显示了在一种2-pentyn-1,6-dione的情况下反应介质对环化反应结果的影响（异环化vs.碳环化）。
• Intramolecular Schmidt Reaction of Vinyl Azides with Cyclic Ketones
  作者：Peng Chen、Chu-Han Sun、Yu Wang、Ying Xue、Chen Chen、Mei-Hua Shen、Hua-Dong Xu

  DOI：10.1021/acs.orglett.8b00395

  日期：2018.3.16

  tethered with a vinyl azide group undergo a Schmidt-hydrolysis sequence to give secondary lactams bearing a ketone side chain. Secondary lactams are obtained in a regioselective manner that is not possible in a conventional Schimdt reaction. In addition to the well-documented C-2 nucleophilicity, the N nucleophilicity of vinyl azide disclosed in this work opens a new direction for reaction invention involving

  与叠氮乙烯基连接的环状酮经过施密特水解序列，得到带有酮侧链的仲内酰胺。仲内酰胺是以区域选择性的方式获得的，这在常规的Schimdt反应中是不可能的。除了有据可证的C-2亲核性，这项工作中公开的叠氮化乙烯基的N亲核性为涉及叠氮化乙烯基的反应发明开辟了新的方向。
• Catalyst component for polymerization of alpha-olefins and process for
  申请人：Mitsubishi Chemical Corporation

  公开号：US06084043A1

  公开（公告）日：2000-07-04

  A catalyst component for the polymerization of alpha-olefins, represented by the following formula [I]: ##STR1## wherein R.sup.1 -R.sup.3 =H, a halogen, a C.sub.1-10 hydrocarbon radical, a Si-containing C.sub.1-18 hydrocarbon radical, or a halogen-containing C.sub.1-10, hydrocarbon radical (provided that R.sup.1 and R.sup.2 cannot be hydrogen at the same time); n=2 to 7; Q=a C.sub.1-20 hydrocarbon radical, a silylene or oligosilylene group having or not having a C.sub.1-20 hydrocarbon radical, a germylene group having or not having a C.sub.1-20 hydrocarbon radical; X and Y=H, a halogen, a C.sub.1-20 hydrocarbon radical, or an O- or N-containing C.sub.1-20 hydrocarbon radical; and M=a transition metal selected from the groups IVB-VIB; a catalyst for the polymerization of alpha-olefins, comprising the catalyst component; and a process for producing alpha-olefin polymers, where use is made of the catalyst. Use of the catalyst will produce alpha-olefin polymers having a high melting point and a high molecular weight in a high yield.

  一种催化剂组分，用于α-烯烃的聚合，其由以下式[I]表示：##STR1## 其中R.sup.1-R.sup.3 = H，卤素，C.sub.1-10烃基，含硅C.sub.1-18烃基，或含卤素的C.sub.1-10烃基（前提是R.sup.1和R.sup.2不能同时为氢）; n = 2至7; Q = C.sub.1-20烃基，具有或不具有C.sub.1-20烃基的硅亚烷或寡硅亚烷基，具有或不具有C.sub.1-20烃基的锗亚烷基; X和Y = H，卤素，C.sub.1-20烃基，或含O或N的C.sub.1-20烃基; M = 从IVB-VIB族选择的过渡金属; 包括催化剂组分的α-烯烃聚合催化剂;以及使用催化剂生产α-烯烃聚合物的过程。使用该催化剂将产生高熔点和高分子量的α-烯烃聚合物，并且产量高。