13-辛基-1,4,7,10-四氧杂-13-氮杂环十五烷 | 142633-89-4

• 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: 13-辛基-1,4,7,10-四氧杂-13-氮杂环十五烷
• 英文名称: (1R,4R)-trans-1-hydroxy-4-<<(tert-butyloxy)carbonyl>amino>-2-cyclopentene
• 英文别名: tert-butyl N-[(1R,4R)-4-hydroxycyclopent-2-en-1-yl]carbamate
• CAS: 142633-89-4
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: UWWUTEZECIYOCW-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  13-辛基-1,4,7,10-四氧杂-13-氮杂环十五烷 在 甲基磺酰氯 、 三乙胺 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,4R)-cis-1-chloro-4-<<(tert-butyloxy)carbonyl>amino>-2-cyclopentene 、 (1R,4R)-trans-1-chloro-4-<<(tert-butyloxy)carbonyl>amino>-2-cyclopentene
  参考文献：
  名称：

  S-(5'-Deoxy-5'-adenosyl)-1-ammonio-4-(methylsulfonio)-2-cyclopentene: a potent, enzyme-activated irreversible inhibitor of S-adenosylmethionine decarboxylase

  摘要：

  The compound S-(5'-deoxy-5'-adenosyl)-1-ammonio-4-(methylsulfonio)-2-cyclopentene (AdoMac) was prepared and evaluated as an irreversible inhibitor of S-adenosylmethionine decarboxylase (AdoMet-DC). AdoMac was shown to inhibit AdoMet-DC in a time-dependent manner with a K(I) of 18.3-mu-M and a k(inact) of 0.133 min-1. In addition, AdoMet-DC activity could not be restored following extensive dialysis of the enzyme-inhibitor complex, and the enzyme was protected from irreversible inactivation by the known competitive inhibitor methylglyoxal bis(guanylhydrazone). HPLC analysis of the enzymatic reaction products revealed a time-dependent decrease in the peak coeluting with AdoMac, and a corresponding increase in the peak coeluting with (methylthio)adenosine (MTA), a byproduct of the irreversible binding of AdoMac to the enzyme. Thus, AdoMac appears to function as an enzyme-activated, irreversible inhibitor of AdoMet-DC.

  DOI：

  10.1021/jm00095a015
• 作为产物：
  描述：

  (SS,R)-(+)-dimethyl [2-oxo-4-(p-toluenesulfinylamino)-hept-5-enyl]-phosphonate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) sodium tetrahydroborate 、 cerium(III) chloride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 13-辛基-1,4,7,10-四氧杂-13-氮杂环十五烷
  参考文献：
  名称：

  Asymmetric Synthesis of the Carbocyclic Nucleoside Building Block (R)-(+)-4-Aminocyclopentenone Using δ-Amino β-Ketophosphonates and Ring-Closing Metathesis (RCM)

  摘要：

  Amino keto-2,7-dienes undergo ring-closing metathesis (RCM) to give 4-aminocyclopentenones, valuable intermediates in the asymmetric construction of carbocyclic nucleosides. The key amino ketodienes were prepared using delta-amino beta-ketophophonates, a new sulfinimine-derived chiral building block, and HWE chemistry.

  DOI：

  10.1021/ol049795v

文献信息

• Addition of Lithium Anion of (Acetylmethylene)triphenylphosphorane to Nonracemic Sulfinimines: Total Synthesis of (+)-241D and Formal Total Synthesis of (+)-Preussin
  作者：Sopan P. Khandare、Polimera Obula Reddy、Kavirayani R. Prasad

  DOI：10.1021/acs.orglett.0c02608

  日期：2020.9.18

  enylphosphorane to nonracemic sulfinimines was investigated. It was found that the addition proceeded with good diastereoselectivity and further reaction of the formed sulfinimidophosphorane with several aldehydes afforded the β-sulfinamido substituted enones in good yields. The resultant enones were elaborated to the synthesis of alkaloid (+)-241D, to the formal total synthesis of (+)-preussin, and

  研究了将（乙酰基亚甲基）三苯基膦烷的锂阴离子加到非外消旋亚氨基亚胺上。发现添加以良好的非对映选择性进行，并且所形成的亚磺酰亚胺基亚膦酰基膦与几种醛的进一步反应以良好的产率提供了β-亚磺酰胺基取代的烯酮。将得到的烯酮详细描述为生物碱（+）-241D的合成，（+）-普鲁酶的正式全合成以及氨基环戊烯醇的合成。