4-[N-(imino{[(phenylmethoxy)carbonyl]amino}methyl)-N-[(phenylmethoxy)carbonyl]amino]butan-1-ol | 150252-67-8

• 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: 4-[N-(imino{[(phenylmethoxy)carbonyl]amino}methyl)-N-[(phenylmethoxy)carbonyl]amino]butan-1-ol
• 英文别名: benzyl N-(4-hydroxybutyl)-N-(N'-phenylmethoxycarbonylcarbamimidoyl)carbamate
• CAS: 150252-67-8
• 化学式: C₂₁H₂₅N₃O₅
• 分子量: 399.447
• InChiKey: WRHDEMCKNDIYPS-UHFFFAOYSA-N

物化性质

• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[N-(imino{[(phenylmethoxy)carbonyl]amino}methyl)-N-[(phenylmethoxy)carbonyl]amino]butan-1-ol 在 4-二甲氨基吡啶 、 哌啶乙酸盐 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 72.0h， 生成 4-(1,3-bis((benzyloxy)carbonyl)guanidino)butyl (6E,11E)-2-hexanoyl-8-oxopentadeca-2,6,11-trienoate
  参考文献：
  名称：

  batzelladine E及其E异构体的合成

  摘要：

  4E的合成确定巴兹拉丁E（4Z）具有Z-而不是先前描述的E-立体化学。Batzelladine E（4Z）已通过有效的9步路线合成，总产率为3％。

  DOI：

  10.1016/s0040-4039(98)01196-4
• 作为产物：
  描述：

  氯甲酸苄酯 、 (4-hydroxybutyl)guanidinium toluenesulfonate 在 三甲基氯硅烷 、 N,N-二异丙基乙胺 作用下， 生成 4-[N-(imino{[(phenylmethoxy)carbonyl]amino}methyl)-N-[(phenylmethoxy)carbonyl]amino]butan-1-ol
  参考文献：
  名称：

  Biomimetic synthesis of (.+-.)-crambines A, B, C1, and C2. Revision of the structure of crambines B and C1

  摘要：

  Crambines A (7) (eight steps, 22%), B (45d) (eight Steps, 19%), C1 (9d) (seven steps, 21%), and C2 (9a) (seven steps, 27%) have been synthesized expediently and stereospecifically by a biomimetic route from methyl acetoacetate. Aminodihydropyrimidines 39 and 40 are formed efficiently from enone ester 36 by a two-step procedure involving addition of O-methylisourea to give methoxydihydropyrimidine 37 followed by displacement of the methoxy group of 37 with ammonia. Hydrogenolysis of 40a and 40d afford crambines C2 and C1, respectively. Mesylation of the alcohol of 39a or 40a followed by Et3N-catalyzed cyclization and hydrogenolysis affords crambine A (7). Aminal formation from 39d or 40d in CHCl3 followed by hydrogenolysis proceeds stereospecifically to provide crambine B (45d). The structure of crambine B has been revised to the stereochemistry shown in 45 and both crambines B and Cl have a seven rather than five-carbon guanidino alkyl chain.

  DOI：

  10.1021/jo00067a014

文献信息

• Synthesis and Determination of Absolute Configuration of the Bicyclic Guanidine Core of Batzelladine A
  作者：Sergio G. Duron、David Y. Gin

  DOI：10.1021/ol015848m

  日期：2001.5.1

  [reaction: see text] The synthesis of a selectively protected form of the bicyclic guanidine fragment of batzelladine A from L-aspartic acid is reported, thereby establishing the absolute configuration of the bicyclic guanidine ring system within the natural product.

  [反应：见正文]据报道，从L-天冬氨酸合成了选择性保护的巴兹拉定A的双环胍片段的形式，从而在天然产物中建立了双环胍环系统的绝对构型。
• Synthesis of (±)-Phloeodictine A1
  作者：Bobbianna J. Neubert、Barry B. Snider

  DOI：10.1021/ol034042e

  日期：2003.3.1

  The antitumor antibiotic phloeodictine A1 (2) has been synthesized by a convergent seven-step route in 8% overall yield. The key step was the Eguchi aza-Wittig reaction of 6 to give 13 followed by a retro Diels-Alder reaction to liberate 5. Addition of 11-dodecenylmagnesium bromide to 5 to give 4b, alkylation with 18b, and deprotection completed the first synthesis of 2.

  抗肿瘤抗生素Phophoodictine A1（2）已通过收敛的七步法合成，总收率为8％。关键步骤是6的Eguchi aza-Wittig反应，得到13，然后进行逆Diels-Alder反应，释放5。将11-十二碳烯溴化镁添加到5，得到4b，用18b烷基化，并脱保护，完成了第一步的合成。 2。
• Biomimetic synthesis of (.+-.)-crambines A, B, C1, and C2. Revision of the structure of crambines B and C1
  作者：Barry B. Snider、Zhongping Shi

  DOI：10.1021/jo00067a014

  日期：1993.7

  Crambines A (7) (eight steps, 22%), B (45d) (eight Steps, 19%), C1 (9d) (seven steps, 21%), and C2 (9a) (seven steps, 27%) have been synthesized expediently and stereospecifically by a biomimetic route from methyl acetoacetate. Aminodihydropyrimidines 39 and 40 are formed efficiently from enone ester 36 by a two-step procedure involving addition of O-methylisourea to give methoxydihydropyrimidine 37 followed by displacement of the methoxy group of 37 with ammonia. Hydrogenolysis of 40a and 40d afford crambines C2 and C1, respectively. Mesylation of the alcohol of 39a or 40a followed by Et3N-catalyzed cyclization and hydrogenolysis affords crambine A (7). Aminal formation from 39d or 40d in CHCl3 followed by hydrogenolysis proceeds stereospecifically to provide crambine B (45d). The structure of crambine B has been revised to the stereochemistry shown in 45 and both crambines B and Cl have a seven rather than five-carbon guanidino alkyl chain.
• Synthesis of batzelladine E and its E isomer
  作者：Barry B. Snider、Jinsheng Chen

  DOI：10.1016/s0040-4039(98)01196-4

  日期：1998.8

  The synthesis of 4E established that batzelladine E (4Z) has the Z- rather than the E-stereochemistry previously depicted. Batzelladine E (4Z) has been synthesized by an efficient 9-step route in 3% overall yield.

  4E的合成确定巴兹拉丁E（4Z）具有Z-而不是先前描述的E-立体化学。Batzelladine E（4Z）已通过有效的9步路线合成，总产率为3％。