methyl 3-acetoxy-5-hexyl-2-methylenepent-4-ynoate | 1332481-22-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-acetoxy-5-hexyl-2-methylenepent-4-ynoate
• 英文别名: methyl 3-acetoxy-2-methyleneundec-4-ynoate
• CAS: 1332481-22-7
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: UXXPXNZZJQUAEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 3-acetoxy-5-hexyl-2-methylenepent-4-ynoate 在 potassium carbonate 、 potassium thioacetate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以70%的产率得到methyl 5-heptylthiophene-3-carboxylate
  参考文献：
  名称：

  硫代苯胺从森田-贝利斯-希尔曼醋酸酯中取代噻吩的硫环化方法

  摘要：

  已开发出一种新的方案，用于在温和且无金属的反应条件下，通过Morita-Baylis-Hillman乙炔醛乙酸盐与硫代乙酸钾的碱促进硫代环化反应，合成串联噻吩取代/去乙酰化5-exo-挖-硫代环异构化。所获得的产物提供了4 H-噻吩并[3，2- c ]亚甲基和噻吩并[3，2- c ]二氢喹啉的入口。

  DOI：

  10.1021/jo400567h
• 作为产物：
  描述：

  non-2-ynal 在 三乙烯二胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 methyl 3-acetoxy-5-hexyl-2-methylenepent-4-ynoate
  参考文献：
  名称：

  Cu(I)-Catalyzed Aminative Aza-Annulation of Enynyl Azide using N-Fluorobenzenesulfonimide: Synthesis of 5-Aminonicotinates

  摘要：

  An unprecedented copper-catalyzed aminative aza-annulation of enynyl azide using commercially available N-fluorobenzenesulfonhnide (NFSI) as an amination reagent is described. The reaction proceeds via regioselective inter-/intramolecular diamination, incorporating one nitrogen from the NFSI and the other from the azide, to provide amino substituted nicotinate derivatives in a single step with moderate to high yield. This method represents an efficient way to access diverse aminonicotinates through direct C-N bond-coupling processes.

  DOI：

  10.1021/acs.orglett.8b01228

文献信息

• Facile Entry to 3,4-Dihydro-1<i>H</i>-pyrrolo[2,1-<i>c</i>][1,4]oxazines through the<i>oxa</i>-Pictet-Spengler Reaction
  作者：Chada Raji Reddy、Amarender Goud Burra、Kiran K. Singarapu、René Grée

  DOI：10.1002/ejoc.201600928

  日期：2016.11

  An intermolecular approach to the construction of 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazines is reported for the first time using the oxa-Pictet–Spengler reaction. The method involves a sequence of carbon–carbon- and carbon–oxygen-bond formation between a substituted 2-(1H-pyrrol-1-yl)ethan-1-ol and an aldehyde/ketone. p-Toluenesulfonic acid (pTSA) was identified as a suitable catalyst to promote the

  首次报道了使用 oxa-Pictet-Spengler 反应构建 3,4-二氢-1H-吡咯并 [2,1-c][1,4] 恶嗪的分子间方法。该方法涉及在取代的 2-(1H-pyrrol-1-yl)ethan-1-ol 和醛/酮之间形成一系列碳-碳和碳-氧键。对甲苯磺酸 (pTSA) 被认为是促进反应的合适催化剂。该方法提供了将各种醛/酮一步转化为相应的 3,4-二氢-1H-吡咯并 [2,1-c][1,4] 恶嗪的方法。© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
• Copper-promoted cascade reaction of active methylenes with MBH-acetates of acetylenic aldehydes to functionalized cyclopentenes
  作者：Chada Raji Reddy、Paridala Kumaraswamy

  DOI：10.1039/c3ra46229c

  日期：——

  One-pot synthesis of substituted cyclopentenes was accomplished through a copper-mediated [4 + 1]-annulation of active methylene compounds with Morita–Baylis–Hillman (MBH) acetates of acetylenic aldehydes. The reaction sequence involves the cascade allylic substitution/5-exo-dig-carbocyclization, which was effective in providing methylene, alkylidene as well as arylidene cyclopentenes.

  通过铜催化的活性次甲基化合物与炔丙醛Morita-Baylis-Hillman（MBH）乙酸酯之间的[4+1]环化反应，成功实现了取代环戊烯的一锅法合成。该反应序列涉及级联亲电性烯丙基取代/5-外向-挖环碳环化反应，对合成次甲基、亚烷基及亚苯基环戊烯均非常有效。
• Morita–Baylis–Hillman acetates of acetylenic aldehydes: versatile synthons for substituted pyrroles via a metal-free tandem reaction
  作者：Chada Raji Reddy、Motatipally Damoder Reddy、Boinapally Srikanth、Kothakonda Rajendra Prasad

  DOI：10.1039/c1ob05402c

  日期：——

  A mild and metal-free access to 1,2,4-tri or 1,2,4,5-tetrasubstituted pyrroles has been developed by the reaction of Morita–Baylis–Hillman acetates of acetylenic aldehydes with amines and sulfonamides. This new protocol is based on K2CO3-promoted tandem allylic substitution/cycloisomerization reactions.

  通过乙炔醛的 MoritaâBaylisâHillman 乙酸酯与胺和磺酰胺的反应，开发出了一种温和、无金属的 1,2,4- 三或 1,2,4,5- 四取代吡咯。这一新方案基于 K2CO3 促进的串联烯丙基取代/环异构化反应。
• Aza-Annulation of Enynyl Azides: A New Approach to Substituted Pyridines
  作者：Chada Raji Reddy、Sujatarani A. Panda、Motatipally Damoder Reddy

  DOI：10.1021/ol503752k

  日期：2015.2.20

  Synthesis of substituted pyridines through a novel aza-annulation of 2-en-4-ynyl azides, derived from MBH-acetates of acetylenic aldehydes, is described. A variety of enynyl azides having aryl, heteroaryl, and alkyl groups on the alkyne functionality successfully participated in the Ag-mediated annulation reaction to provide the corresponding 3,6-disubstituted pyridines. I2-Mediated cyclization was

  描述了通过衍生自炔醛的MBH-乙酸酯的新的2-en-4-炔基叠氮化物的氮杂-环烷基合成取代的吡啶。在炔官能团上具有芳基，杂芳基和烷基的各种烯丙基叠氮化物成功地参与了Ag介导的环化反应，以提供相应的3，6-二取代的吡啶。发现I 2-介导的环化受到炔官能团上的取代基的控制，所述取代基由炔炔官能团上具有富电子取代基的烯丙基叠氮化物提供了5-碘-3，6-二取代的吡啶。
• Synthesis of substituted 3-furanoates from MBH-acetates of acetylenic aldehydes via tandem isomerization–deacetylation–cycloisomerization: access to Elliott's alcohol
  作者：Chada Raji Reddy、Gaddam Krishna、Motatipally Damoder Reddy

  DOI：10.1039/c3ob42396d

  日期：——

  A new method for the synthesis of 5-substituted furan-3-carboxylates from Morita–Baylis–Hillman acetates of acetylenic aldehydes is reported. The process involves palladium-catalyzed isomerization followed by base-promoted deacetylation and cycloisomerization reactions. The utility of this chemistry is further demonstrated by the synthesis of Elliott's alcohol, a key intermediate of the pyrethroid resmethrins.

  报告了一种从乙炔醛的 MoritaâBaylisâHillman 乙酸酯合成 5-取代呋喃-3-羧酸酯的新方法。该过程包括钯催化异构化，然后进行碱促进的脱乙酰化和环异构化反应。通过合成埃利奥特醇（一种拟除虫菊酯类化合物除虫菊酯的关键中间体），进一步证明了这种化学方法的实用性。