-(4-hydroxy-1,3-dimethyl-2-butenyl)carbamic acid tert-butyl ester | 109986-62-1

• 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
• 英文名称: -(4-hydroxy-1,3-dimethyl-2-butenyl)carbamic acid tert-butyl ester
• 英文别名: (R-(E))-(4-hydroxy-1,3-dimethyl-2-butenyl)carbamic acid tert-butyl ester；tert-butyl N-[(E,2R)-5-hydroxy-4-methylpent-3-en-2-yl]carbamate
• CAS: 109986-62-1
• 化学式: C₁₁H₂₁NO₃
• 分子量: 215.293
• InChiKey: XNJNRYOFWDGDDG-BNICOGTQSA-N

物化性质

• 沸点：
  334.5±35.0 °C(Predicted)
• 密度：
  1.007±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  -(4-hydroxy-1,3-dimethyl-2-butenyl)carbamic acid tert-butyl ester 在 盐酸 作用下， 反应 1.0h， 生成 (E)-(R)-4-Amino-2-methyl-pent-2-en-1-ol
  参考文献：
  名称：

  Purines. XXXIII. Syntheses and cytokinin activities of both enantiomers of 1'-methylzeatin and their 9-.BETA.-D-ribofuranosides.

  摘要：

  由 Pseudomonas syringae pv savastanoi 分泌的细胞分裂素 1'-methylzeatin 及其 9-riboside 的结构和绝对构型已被确定，分别为 [R-(E)]-2-甲基-4-(9H-嘌呤-6-基氨基)-2-戊烯-1-醇[(1'R)-2]和 [R-(E)]-N-(4-羟基-1、(1'R)-和(1'S)-1'-甲基玉米素[(1'R)-2 和 (1'S)-2]及其 9-β-D-ribofuranosides [(1'R)-4和 (1'S)-4]的手性合成。这些玉米素衍生物在烟草胼胝体和莴苣种子萌发生物测定中进行了细胞分裂素活性测试。结果发现，"天然 "对映体（1'R）-2 的活性与玉米素（1）本身相同，而且比其 9-核苷[（1''R）-4]的活性更高。非天然 "对映体（1'S）-2 及其 9-核苷[(1''S)-4]的活性分别低于相应的天然细胞分裂素（1'R）-2 和 (1''R)-4）。

  DOI：

  10.1248/cpb.37.1758
• 作为产物：
  描述：

  (2E,4R)-4-(tert-butoxycarbonylamino)-2-methyl-2-pentenoic acid 在 sodium tetrahydroborate 、 氯甲酸乙酯 、 三乙胺 作用下， 生成 -(4-hydroxy-1,3-dimethyl-2-butenyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  细胞分裂素1'-甲基玉米素及其9-核糖苷的合成及绝对构型

  摘要：

  上（1'的手性合成的基础- [R）-1和（1'小号）-I和其9- ribosides（1“ - [R）-III和（1”小号）-III从d -和大号-丙氨酸，细胞分裂素1'- methylzeatin和其9-核糖核苷的结构已经被确定为（1' - [R）-1和（1“ - [R）-III。

  DOI：

  10.1016/s0040-4039(00)87806-5

文献信息

• Purines. LXII. Both Enantiomers of N6-(1,3-Dimethyl-2-butenyl)adenine and Their 9-.BETA.-D-Ribofuranosides: Synthesis and Cytokinin Activity.
  作者：Tozo FUJII、Masashi OHBA、Hitoshi KAWAMURA、Yoshiyuki NAKASHIO、Kei HONDA、Satoshi MATSUBARA

  DOI：10.1248/cpb.42.1045

  日期：——

  Both enantiomers [(1'R)-6 and (1'S)-6] of N6-(1, 3-dimethyl-2-butenyl)adenine and their 9-β-D-ribofuranosides [(1"R)-16 and (1"S)-16] have been synthesized for the first time from both enantiomers of alanine (15) in nine steps. These aglycones and nucleosides, together with N6-(3-methyl-2-butenyl)adenine (5) and its 9-β-D-ribofuranoside (18) as well as 9-β-D-ribofuranosyl-cis-zeatin (20) and 9-(2-deoxy-β-D-ribofuranosyl)-cis-zeatin (19), were tested for cytokinin activity in the tobacco callus bioassay. The order of their activity was 5>(1'R)-6>(1"R)-16≈18>(1'S)-6>(1"S)-16>20>19. The bioassay results are compared with those obtained previously for the derivatives modified analogously in the N6-substituent in the cis- and trans-zeatin series.

  N6-(1, 3-二甲基-2-丁烯基)腺嘌呤的两种对映体 [(1'R)-6 和 (1'S)-6] 及其 9-β-D-呋喃核苷 [(1"R)-16 和(1"S)-16] 首次通过九个步骤从丙氨酸 (15) 的两种对映体合成。这些苷元和核苷，以及 N6-(3-甲基-2-丁烯基)腺嘌呤 (5) 及其 9-β-D-呋喃核苷 (18) 以及 9-β-D-呋喃核糖基-顺式-玉米素 (20) ) 和 9-(2-脱氧-β-D-呋喃核糖基)-顺式-玉米素 (19) 在烟草愈伤组织生物测定中测试了细胞分裂素活性。它们的活性顺序为5>(1'R)-6>(1”R)-16&18>(1'S)-6>(1”S)-16>20>19。将生物测定结果与先前获得的顺式和反式玉米素系列的N6-取代基中类似修饰的衍生物的生物测定结果进行比较。
• Purines. LV. Syntheses and Cytokinin Activities of Some Adenine and Adenosine Derivatives Related to 1'-Methylzeatin.
  作者：Tozo FUJII、Masashi OHBA、Hitoshi KAWAMURA、Tsuyoshi HANEISHI、Satoshi MATSUBARA

  DOI：10.1248/cpb.41.1362

  日期：——

  (1'S)-1-Methyl-cis-zeatin [(1'S)-2] and its 9-β-D-ribofuranoside [(1"S)-4] were synthesized from L-alanine through [S-(Z)]-4-amino-2-methyl-2-penten-1-ol ethanedioate [(S)-3]. Condensations of 2-hydroxy-6-methylthiopurine (16) with the trans-isomeric amine salt [(S)-15], its enantiomer [(R)-15], and the racemic modification [(±)-15] furnished (1'S)-, (1'R)-, and (±)-2-hydroxy-1'-methyl-trans-zeatine (6), respectively. A similar condensation of 16 with methylamine yielded 2-hydroxy-N6-methyladenine (7). These adenine derivatives were tested for cytokinin activity in the tobacco callus bioassay, and the order of their activity was (1'R)-6>(±)-6>(1'S)-2>7; on the other hand, (1"S)-4 and (1'S)-6 were completely inactive at 0.1-100μM and 0.01-10μM concentrations, respectively. As a result of the above syntheses of (1'R)-6, (1'S)-6, (±)-6, and 7, the gross structures of a marine green alga cytokinin and of a blue coral cytokinin were established to be 6 and 7, respectively.

  以L-丙氨酸为原料，通过[S-(Z)]合成(1'S)-1-甲基-顺式玉米素[(1'S)-2]及其9-β-D-呋喃核苷[(1"S)-4] -4-氨基-2-甲基-2-戊烯-1-醇乙二酸酯[(S)-3] 2-羟基-6-甲基硫嘌呤(16)与反式异构胺盐[(S)-15]、其对映体[(R)-15]和外消旋体[(±)-15]提供(1'S)-、(1'R)-和(± )-2-羟基-1'-甲基-反式-玉米丁(6)，分别用甲胺进行类似的缩合，得到2-羟基-N6-甲基腺嘌呤(7)。烟草愈伤组织生物测定中的细胞分裂素活性，其活性顺序为(1'R)-6>(±)-6>(1'S)-2>7；另一方面，(1"S)-4和(1'S)-6 分别在 0.1-100μM 和 0.01-10μM 浓度下完全失活。作为(1'R)-6、(1'S)-6、(±)-6和7的上述合成的结果，海洋绿藻细胞分裂素和蓝珊瑚细胞分裂素的总体结构被确定为分别为6和7。
• Synthesis and Absolute Configuration of the Green Alga Cytokinin 2-Hydroxy-1'-methylzeatin
  作者：Tozo Fujii、Masashi Ohba、Tsuyoshi Haneishi、Satoshi Matsubara、A. H. Abad Farooqi、Y. N. Shukla

  DOI：10.3987/com-91-5920

  日期：——

  The correctness of the gross structure of the marine green alga cytokinin 2-hydroxy-1'-methylzeatin (1) has been confirmed as a result of the chiral syntheses of (1'R)-1 and (1'S)-1. An indirect comparison of the cytokinin activity of the natural cytokinin with those of the synthetic enantiomers suggests that the R configuration may be assigned to the natural one unless it would be racemic.
• FUJII, TOZO;ITAYA, TAISUKE;MATSUBARA, SATOSHI, CHEM. AND PHARM. BULL., 37,(1989) N, C. 1758-1763
  作者：FUJII, TOZO、ITAYA, TAISUKE、MATSUBARA, SATOSHI

  DOI：——

  日期：——