2-methyl-3-[4-methyl(3,5-oxazolyl)]prop-2-en-1-ol | 147438-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-3-[4-methyl(3,5-oxazolyl)]prop-2-en-1-ol
• 英文别名: (E)-2-methyl-3-(2-methyl-oxazol-4-yl)-prop-2-en-1-ol；2-Methyl-3-(2-methyl(1,3-oxazolyl))-propenol；(E)-2-methyl-3-(2-methyl-1,3-oxazol-4-yl)prop-2-en-1-ol
• CAS: 147438-69-5
• 化学式: C₈H₁₁NO₂
• 分子量: 153.181
• InChiKey: GJJQUKGVWVCDSC-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-3-[4-methyl(3,5-oxazolyl)]prop-2-en-1-ol 在 sodium periodate 、 N-溴代丁二酰亚胺(NBS) 、 2-甲基-2-丁烯 、 双(三甲基硅烷基)氨基钾 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 1.16h， 生成
  参考文献：
  名称：

  The first total synthesis of the antitumor macrolide, rhizoxin

  摘要：

  The first total synthesis of the antitumor macrolide, rhizoxin in a highly stereocontrolled manner is described.

  DOI：

  10.1016/s0040-4039(00)77486-7
• 作为产物：
  描述：

  2-甲基-4-恶唑甲醇 在 草酰氯 、 TEA 、 potassium tert-butylate 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.58h， 生成 2-methyl-3-[4-methyl(3,5-oxazolyl)]prop-2-en-1-ol
  参考文献：
  名称：

  The first total synthesis of the antitumor macrolide, rhizoxin

  摘要：

  The first total synthesis of the antitumor macrolide, rhizoxin in a highly stereocontrolled manner is described.

  DOI：

  10.1016/s0040-4039(00)77486-7

文献信息

• Synthetic Studies of Antitumor Macrolide Rhizoxin:  Stereoselective Syntheses of the C(1)−C(9) and C(12)−C(26) Subunits
  作者：Steven D. Burke、Jian Hong、Joseph R. Lennox、Andrew P. Mongin

  DOI：10.1021/jo980754k

  日期：1998.10.1

  Horner-Wadsworth-Emmons reaction. The central segment 4 and the oxazole chromophore side chain 3 were coupled using another highly stereoselective Horner-Wadsworth-Emmons reaction. Two different lactone subunits [C(1)-C(9) segment 5 and C(3)-C(10) segment 47] were also prepared, employing a thermodynamically controlled diastereotopic group differentiation tactic for establishing the C(5) stereochemistry

  描述了一种三重收敛的合成方法，该方法最终完成了大环内酯类抗肿瘤剂Rhizoxin的C（1）-C（9）和C（12）-C（26）亚基的对映选择性合成。中央C（12）-C（20）亚基4是通过猪胰脂肪酶的非对映选择性酶促乙酸15水解，螯合控制的爱尔兰-克莱森重排（10-> 12）结合动力学溴化（12）有效制备的（12） -> 14）和Mitsunobu反演（23-> 26），以引入三个连续的C（15）-C（17）立体中心。C（18）-C（19）三取代（E）-烯烃的形成是通过立体选择性Horner-Wadsworth-Emmons反应实现的。使用另一个高度立体选择性的霍纳-沃兹沃思-埃蒙斯反应将中心链段4和恶唑生色团侧链3偶联。
• Selective Lithiation of 2-Methyloxazoles. Applications to Pivotal Bond Constructions in the Phorboxazole Nucleus
  作者：David A. Evans、Victor J. Cee、Thomas E. Smith、Keith J. Santiago

  DOI：10.1021/ol990027r

  日期：1999.7.1

  The lithiation of 2-methyloxazoles with alkyllithium and hindered lithium amide bases generally results in the competitive formation of a mixture of 5-lithio- and 2-(lithiomethyl)oxazole isomers. Herein a synthetically useful lithiation method which allows for the selective formation of 2-(lithiomethyl)oxazole is described. Diethylamine has been found to be a kinetically competent proton source that will mediate the equilibration of the kinetically formed 5-lithiooxazole to its more stable 2-(lithiomethyl)oxazole counterpart. Application of this metalation strategy with lithium diethylamide to two important bond constructions relevant to a projected phorboxazole synthesis is presented.
• Oxidative Rearrangements of Isobenzofurans: Studies toward the Synthesis of the Ajudazols
  作者：Stephen J. Hobson、Andrew Parkin、Rodolfo Marquez

  DOI：10.1021/ol8009336

  日期：2008.7.3

  We present a new facet of isobenzofuran chemistry which allows for its efficient manipulation to generate biologically relevant entities. This methodology has been successfully applied toward the synthesis of ajudazol A.
• Stereoselective syntheses of the rhizoxin C(1)C–(9) and C(12)–C(26) subunits
  作者：Steven D. Burke、Jian Hong、Andrew P. Mongin

  DOI：10.1016/s0040-4039(98)00268-8

  日期：1998.4

  Stereoselective syntheses of the C(1)-C(9) and C(12)-C(26) subunits of the macrolide antitumor agent rhizoxin are described. Chelation-controlled Ireland-Claisen rearrangement, stereoselective Horner-Wadsworth-Emmons reactions and a thermodynamically-controlled diastereotopic group differentiation are featured. (C) 1998 Elsevier Science Ltd. All rights reserved.
• The first total synthesis of the antitumor macrolide, rhizoxin
  作者：Masahisa Nakada、Susumu Kobayashi、Masakatsu Shibasaki、Shigeo Iwasaki、Masaji Ohno

  DOI：10.1016/s0040-4039(00)77486-7

  日期：1993.2

  The first total synthesis of the antitumor macrolide, rhizoxin in a highly stereocontrolled manner is described.