methyl 5-benzyloxy-2-pentynoate | 292631-98-2

• 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: methyl 5-benzyloxy-2-pentynoate
• 英文别名: methyl 1-benzyloxybut-3-ynecarboxylate；5-benzyloxy-pent-2-ynoic acid methyl ester；methyl 5-(benzyloxy)pent-2-ynoate；Yhkddccouspefj-uhfffaoysa-；methyl 5-phenylmethoxypent-2-ynoate
• CAS: 292631-98-2
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: YHKDDCCOUSPEFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  335.5±25.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5-benzyloxy-2-pentynoate 在 二异丁基氢化铝 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 3.0h， 生成 5-benzyloxy-2-pentyn-1-ol
  参考文献：
  名称：

  阳离子铂（II）催化简洁合成两种具有角氧官能度的融合碳环化合物的有效控制

  摘要：

  双重麻烦：从容易获得的底物开始，实现了一种有效的方法，用于制备两种类型的具有角氧官能度的合成有用的双环[5.4.0]十一烷。此方法基于含铂的羰基内酯的[3 + 2]环加成反应（请参阅示意图； R 1 =烷基或烷氧基，R 2 =烷基，R 3 =烷基或乙烯基）。

  DOI：

  10.1002/asia.201100460
• 作为产物：
  描述：

  溴甲苯 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 9.08h， 生成 methyl 5-benzyloxy-2-pentynoate
  参考文献：
  名称：

  Acid-Catalyzed Synthesis of Bicyclo[3.n.1]alkenediones

  摘要：

  An acid-catalyzed Dieckmann-type reaction has been developed to access functionalized bicyclo[3.2.1]alkenediones. This methodology has been successfully extended to more substituted and larger ring homologues, providing a new and efficient route to the core of numerous attractive natural products and their analogues.

  DOI：

  10.1021/ol102909t

文献信息

• Pd-Catalyzed Sulfinylzincation of Activated Alkynes with 1-Alkynyl Sulfoxides as a Sulfinyl Source
  作者：Naoyoshi Maezaki、Suguru Yagi、Ryoko Yoshigami、Jun Maeda、Tomoko Suzuki、Shizuka Ohsawa、Kouji Tsukamoto、Tetsuaki Tanaka

  DOI：10.1021/jo034108j

  日期：2003.7.1

  with 1-alkynyl sulfoxide as a sulfinyl source was developed. Bis-sulfinyl alkenes were formed in good yields on treatment of 1-alkynyl sulfoxides with Et(2)Zn in the presence of a Pd-catalyst, wherein zinc sulfenate (or sulfinylzinc) species would be generated in situ to undergo highly syn-selective conjugate addition to the 1-alkynyl sulfoxides. By using 3,3-dimethyl-1-butynyl sulfoxides, formation of

  开发了前所未有的Pd催化的亚砜基1-炔基亚砜催化的亚磺酰基锌化反应。在Pd催化剂存在下，用Et（2）Zn处理1-炔基亚砜时，高产率地形成了双亚磺酰基烯烃，其中，亚硫酸锌（或亚磺酰基锌）物质将在原位生成，以进行高度同位选择性共轭加成至1-炔基亚砜。通过使用3，3-二甲基-1-丁炔基亚砜，完全抑制了双亚磺酰基烯烃的形成，并且实现了活化炔烃的亚磺酰基锌化。该反应耐受各种功能，并且由于炔烃的δ位处杂原子的相邻基团的参与而大大促进了该反应。
• Use of π-allyltricarbonyliron lactone complexes in the synthesis of taurospongin A: a potent inhibitor of DNA polymerase β and HIV reverse transcriptase
  作者：Christopher J. Hollowood、Shigeo Yamanoi、Steven V. Ley

  DOI：10.1039/b301676p

  日期：——

  The total synthesis of taurospongin A by two new approaches has been achieved where π-allyltricarbonyliron lactone complexes have been used to control highly stereoselective additions of the nucleophiles to a carbonyl unit located in the side chain of these complexes.

  已通过两种新方法成功合成了taurospongin A，其中使用了π-烯丙基三羰基铁内酯复合物来控制亲核试剂对这些复合物侧链中碳基单位的高立体选择性加成。
• Enantioselective Synthesis of (2<i>S</i>,3<i>R</i>)-3-Hydroxy-3-methylproline, A Novel Amino Acid Found in Polyoxypeptins
  作者：Dong-Guang Qin、Hui-Yan Zha、Zhu-Jun Yao

  DOI：10.1021/jo016227+

  日期：2002.2.1

  The enantioselective synthesis of (2S,3R)-3-hydroxy-3-methylproline (3) was achieved by the Sharpless AD, regioselective opening of cyclic sulfate by NaN(3) and intramolecular ring-closing reaction. The reported route has the advantage of a high overall yield and good enantiomeric purity, as well as starting from readily available chemical substrates and inexpensive reagents.

  （2S，3R）-3-羟基-3-甲基脯氨酸（3）的对映体选择性合成是通过Sharpless AD，NaN（3）的环硫酸盐的区域选择性开放和分子内闭环反应实现的。所报道的路线的优点是具有高的总产率和良好的对映体纯度，以及从容易获得的化学底物和廉价的试剂开始。
• Golden opportunities in natural product synthesis: first total synthesis of (−)-isocyclocapitelline and (−)-isochrysotricine by gold-catalyzed allene cycloisomerization
  作者：Frank Volz、Norbert Krause

  DOI：10.1039/b703995f

  日期：——

  The first enantioselective total syntheses of the β-carboline alkaloids (–)-isochrysotricine (1) and (–)-isocyclocapitelline (2) are reported which confirm the absolute configuration of these natural products. Key steps are the copper-mediated SN2′-substitution of propargyl oxiranes13/14 and the gold-catalyzed cycloisomerization of α-hydroxyallene 15, resulting in a highly efficient center-to-axis-to-center chirality transfer.

  β-咔啉生物碱 (α)-isochrysotricine (1) 和 (α)-isocyclocapitelline (2) 的第一个对映选择性全合成被报道，证实了这些天然产物的绝对构型。关键步骤是铜介导的炔丙基环氧乙烷13/14的SN2-取代和金催化的α-羟基丙二烯15的环异构化，从而产生高效的中心到轴到中心的手性转移。
• Gold catalysis in stereoselective natural product synthesis: (+)-linalool oxide, (−)-isocyclocapitelline, and (−)-isochrysotricine
  作者：Frank Volz、Sipke H. Wadman、Anja Hoffmann-Röder、Norbert Krause

  DOI：10.1016/j.tet.2008.11.104

  日期：2009.2

  A stereoselective synthesis of the tetrahydrofuran-containing natural products (2S,5R)-(+)-linalool oxide (1), (-)-isocyclocapitelline (2), and (-)-isochrysotricine (3) is reported. Key steps are the copper-mediated S(N)2'-substitution of propargyl oxiranes 7 and the gold-catalyzed cycloisomerization of dihydroxyallenes 8/17, resulting in a highly efficient center-to-axis-to-center chirality transfer. The enantioselective total synthesis of (-)-isocyclocapitelline (2) and (-)-isochrysotricine (3) allowed the elucidation of the absolute configuration of these beta-carboline natural products. (C) 2008 Elsevier Ltd. All rights reserved.

表征谱图