1-((S)-2-Allyloxy-4-methyl-pent-4-enyloxymethyl)-4-methoxy-benzene | 372511-49-4

• 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: 1-((S)-2-Allyloxy-4-methyl-pent-4-enyloxymethyl)-4-methoxy-benzene
• 英文别名: 1-methoxy-4-[[(2S)-4-methyl-2-prop-2-enoxypent-4-enoxy]methyl]benzene
• CAS: 372511-49-4
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: VXYCPYPPHLVCOT-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-((S)-2-Allyloxy-4-methyl-pent-4-enyloxymethyl)-4-methoxy-benzene 在 Grubbs catalyst first generation 、 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 (2S)-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-methanol
  参考文献：
  名称：

  Stereoselective Synthesis of the C13-C28 Subunit of (-)-Laulimalide Utilizing an α-Chlorosulfide Intermediate

  摘要：

  A stereoselective route to the C13-C28 subunit of (-)-laulimalide is described. l-Tartaric acid is the source of the hydroxy groups at C19 and C20. An -chlorosulfide is employed as the key intermediate for the creation of the C17-C18 bond and the C16-C17 double bond was introduced using the Mislow-Braverman rearrangement and Hutchin's dexoxygenation with concomitant double bond transposition reaction. The C15 and C23 stereogenic centers were created using catalytic asymmetric reactions. The trisubstituted and trans-disubstituted alkenes were created stereoselectively by taking advantage of ring-closing metathesis and the Julia-Kocienski olefination reaction, respectively.

  DOI：

  10.1055/s-0033-1339493
• 作为产物：
  描述：

  (Z)-1,4-bis((4-methoxybenzyl)oxy)but-2-ene 在 titanium(IV) isopropylate 、 四氧化锇 、 S-1,1'-联-2-萘酚 、 sodium hydride 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 nujol 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 72.75h， 生成 1-((S)-2-Allyloxy-4-methyl-pent-4-enyloxymethyl)-4-methoxy-benzene
  参考文献：
  名称：

  Stereoselective Synthesis of the C13-C28 Subunit of (-)-Laulimalide Utilizing an α-Chlorosulfide Intermediate

  摘要：

  A stereoselective route to the C13-C28 subunit of (-)-laulimalide is described. l-Tartaric acid is the source of the hydroxy groups at C19 and C20. An -chlorosulfide is employed as the key intermediate for the creation of the C17-C18 bond and the C16-C17 double bond was introduced using the Mislow-Braverman rearrangement and Hutchin's dexoxygenation with concomitant double bond transposition reaction. The C15 and C23 stereogenic centers were created using catalytic asymmetric reactions. The trisubstituted and trans-disubstituted alkenes were created stereoselectively by taking advantage of ring-closing metathesis and the Julia-Kocienski olefination reaction, respectively.

  DOI：

  10.1055/s-0033-1339493

文献信息

• Total Synthesis of the Microtubule-Stabilizing Agent (−)-Laulimalide
  作者：Ian Paterson、Chris De Savi、Matthew Tudge

  DOI：10.1021/ol010150u

  日期：2001.10.1

  [structure: see text] The total synthesis of the potent microtubule-stabilizing anticancer agent (-)-laulimalide has been achieved in 27 steps and 2.9% overall yield. Notable features are the use of Jacobsen HDA chemistry for the enantioselective construction of the side chain dihydropyran, a diastereoselective aldol coupling using chiral boron enolate methodology, a Mitsunobu macrolactonization, and

  [结构：见正文]高效的微管稳定抗癌剂（-）-月桂酰亚胺的总合成已通过27个步骤完成，总产率为2.9％。显着特征是使用Jacobsen HDA化学方法对侧链二氢吡喃进行对映选择性构建，使用手性硼烯醇盐方法进行非对映选择性羟醛偶联，Mitsunobu巨内酯化和Sharpless AE将环氧化物引入去环氧月桂酰亚胺中。