2-甲基-2-丙基[(3S)-2-亚甲基-3-氧杂环丁基]氨基甲酸酯 | 213338-89-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-甲基-2-丙基[(3S)-2-亚甲基-3-氧杂环丁基]氨基甲酸酯
• 英文名称: (S)-3-(tert-butoxycarbonylamino)-2-methyleneoxetane
• 英文别名: tert-butyl N-[(3S)-2-methylideneoxetan-3-yl]carbamate
• CAS: 213338-89-7
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: YIGGATNEKMLTAP-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-2-丙基[(3S)-2-亚甲基-3-氧杂环丁基]氨基甲酸酯 在 二甲基二环氧乙烷 、 lithium 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 N-叔-丁基氧羰基-D-赤式-二氢-D-鞘氨醇
  参考文献：
  名称：

  Synthesis of d-erythro-Dihydrosphingosine and d-xylo-Phytosphingosine from a Serine-Derived 1,5-Dioxaspiro[3.2]hexane Template

  摘要：

  [GRAPHICS]A serine-derived 1,5-dioxaspiro[3,2]hexane template is shown to be a useful precursor for both aminodiol and aminotriol sphingoid bases by its conversion to D-erythro-dihydrosphingosine and D-xylo-phytoshingosine.

  DOI：

  10.1021/ol0200448
• 作为产物：
  描述：

  (S)-α-Boc-氨基-β-丙内酯 、 alkaline earth salt of/the/ methylsulfuric acid 以 甲苯 为溶剂， 反应 4.0h， 以45%的产率得到2-甲基-2-丙基[(3S)-2-亚甲基-3-氧杂环丁基]氨基甲酸酯
  参考文献：
  名称：

  Synthesis of d-erythro-Dihydrosphingosine and d-xylo-Phytosphingosine from a Serine-Derived 1,5-Dioxaspiro[3.2]hexane Template

  摘要：

  [GRAPHICS]A serine-derived 1,5-dioxaspiro[3,2]hexane template is shown to be a useful precursor for both aminodiol and aminotriol sphingoid bases by its conversion to D-erythro-dihydrosphingosine and D-xylo-phytoshingosine.

  DOI：

  10.1021/ol0200448

文献信息

• Preparation and Properties of 2-Methyleneoxetanes
  作者：Lisa M. Dollinger、Albert J. Ndakala、Mehrnoosh Hashemzadeh、Gan Wang、Ying Wang、Isamir Martinez、Joel T. Arcari、David J. Galluzzo、Amy R. Howell、Arnold L. Rheingold、Joshua S. Figuero

  DOI：10.1021/jo9906072

  日期：1999.9.1

  The methylenation of beta-lactones 5 with dimethyltitanocene provides a versatile, reliable, and highly chemoselective entry to 2-methyleneoxetanes 7. The conversion proceeds selectively in the presence of alkenes, unprotected alcohols, and a variety of other carbonyl moieties, A study of conditions for the optimization of this reaction is delineated. In addition, the first X-ray structure of a 2-methyleneoxetane, which shows its similarity to related p-lactones, is reported. Reactivity studies of 2-methyleneoxetanes are presented in which it is demonstrated that these compounds are attacked at C-4 with a nucleophile; then, subsequently, the resultant enolate reacted with an electrophile. An interesting dichotomy of reactivity was observed when methyleneoxetane 7c was treated with electrophiles. Reaction of 7c with acetic acid gave acetoxyoxetane 19. When 7c was exposed to bromine, dibromoketone 20 resulted.
• The First General Synthesis of 1,5-Dioxaspiro[3.2]hexanes
  作者：Albert J. Ndakala、Amy R. Howell

  DOI：10.1021/jo981309s

  日期：1998.9.1
• Synthesis of <scp>d</scp>-<i>e</i><i>rythro</i>-Dihydrosphingosine and <scp>d</scp>-<i>x</i><i>ylo</i>-Phytosphingosine from a Serine-Derived 1,5-Dioxaspiro[3.2]hexane Template
  作者：Albert J. Ndakala、Mehrnoosh Hashemzadeh、Regina C. So、Amy R. Howell

  DOI：10.1021/ol0200448

  日期：2002.5.1

  [GRAPHICS]A serine-derived 1,5-dioxaspiro[3,2]hexane template is shown to be a useful precursor for both aminodiol and aminotriol sphingoid bases by its conversion to D-erythro-dihydrosphingosine and D-xylo-phytoshingosine.
• Synthesis of <i>epi</i>-Oxetin via a Serine-Derived 2-Methyleneoxetane
  作者：Marisa L. Blauvelt、Amy R. Howell

  DOI：10.1021/jo7018762

  日期：2008.1.1

  [GRAPHICS]The unique reactivity of 2-methyleneoxetanes and 1,5-dioxaspiro[3.2]hexanes has been exploited for the synthesis of epi-oxetin (26), an oxetane-containing beta-amino acid. While the preparation of the natural product oxetin (1) was the original goal, the unexpected diastereoselectivity of an precedented reduction provided the epi-oxetin framework. The methodology described herein should be amenable for the preparation of oxetin with a change in nitrogen protection.