(1R,4S)-N-butyryl-1-amino-4-(hydroxymethyl)-2-cyclopentene

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (1R,4S)-N-butyryl-1-amino-4-(hydroxymethyl)-2-cyclopentene
• 英文别名: (1R,4S)-1-butyrylamino-4-(hydroxymethyl)-2-cyclopentene；N-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl]butanamide
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: PVRSHAUROLANIJ-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  丁酰氯 、 (1S,4R)-(4-氨基环戊-2-烯基)甲醇盐酸盐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到(1R,4S)-N-butyryl-1-amino-4-(hydroxymethyl)-2-cyclopentene
  参考文献：
  名称：

  Process for the preparation of aminoalcohol derivatives and their further conversion to (1R, 4S)-4-((2-amino-6-chloro-5-formamido-4-pyrimidinyl)-amino)-2-cyclopentenyl-1- methanol

  摘要：

  该发明涉及一种新颖的方法，用于制备公式1的氨基醇，其为外消旋或光学活性，从2-azabi-cyclo［2.2.1］hept-5-en-3-one出发，进一步转化为相应的酰基衍生物，再进一步转化为公式2中的(1S,4R)-或(1R,4S)-4-(2-氨基-6-氯-9-H-嘌呤-9-基)-2-环戊烯基-1-甲醇。在后一合成中，氨基醇转化为相应的D-或L-酒石酸盐，然后与公式3中的N-(2-氨基-4,6-二氯嘧啶-5-基)甲酰胺反应，以得到公式4中的(1S,4R)-或(1R,4S)-4-(2-氨基-6-氯-5-甲酰胺基-4-嘧啶基)氨基-2-环戊烯基-1-甲醇，然后进行环化反应以得到最终的化合物。

  公开号：

  US20020010360A1

文献信息

• Process for the preparation of aminoalcohol derivatives and their further conversion to (1R,4S)-4-(2-amino-6-chloro-5-formamido-4-pyrimidinyl)-amino)-2-cyclopentenyl-1-methanol
  申请人：——

  公开号：US20040142436A1

  公开（公告）日：2004-07-22

  The invention relates to a novel process for the preparation of an aminoalcohol of the formula 1 racemically or optically active, starting from 2-azabicyclo[2.2.1]hept-5-en-3-one, its further conversion to give the corresponding acyl derivative and its further conversion to (1S,4R)- or (1R,4S)-4-(2-amino-6-chloro-9-H-purine-9-yl)-2-cyclopentenyl-1-methanol of the formulae 2 In the latter synthesis, the aminoalcohol is converted into the corresponding D- or L-tartrate, which is then reacted with N-(2-amino-4,6-dichloropyrimidin-5-yl) form amide of the formula 3 to give (1S,4R)- or (1R,4S)-4-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2-cyclopentenyl-1-methanol of the formulae 4 and then cyclized to give the end compounds.

  本发明涉及一种从2-氮杂双环[2.2.1]庚-5-烯-3-酮出发制备公式1的氨基醇的新工艺，其进一步转化为相应的酰基衍生物，并进一步转化为公式2的(1S,4R)-或(1R,4S)-4-(2-氨基-6-氯-9-H-嘌呤-9-基)-2-环戊基-1-甲醇。在后一种合成中，氨基醇转化为相应的D-或L-酒石酸盐，然后与公式3的N-(2-氨基-4,6-二氯嘧啶-5-基)甲酰胺反应，以给出公式4的(1S,4R)-或(1R,4S)-4-[(2-氨基-6-氯-5-甲酰基-4-嘧啶基)氨基]-2-环戊基-1-甲醇，然后环化以得到最终产物。
• PROCESS FOR THE PREPARATION OF AMINOALCOHOL DERIVATIVES AND THEIR FURTHER CONVERSION TO (1R, 4S)-4(2-AMINO-6-CHLORO-5-FORMAMIDO-4- PYRIMIDINYL)-AMINO-2-CYCLOPENTENYL-1-METHANOL
  申请人：Brieden Walter

  公开号：US20060211862A1

  公开（公告）日：2006-09-21

  The invention relates to a novel process for the preparation of an aminoalcohol of the formula racemically or optically active, starting from 2-azabicyclo[2.2.1]hept-5-en-3-one, its further conversion to give the corresponding acyl derivative and its further conversion to (1S,4R)- or ( 1 R,4S)-4-(2-amino-6-chloro-9-H-purine-9-yl)-2-cyclopentenyl-1-methanol of the formulae In the latter synthesis, the aminoalcohol is converted into the corresponding D- or L-tartrate, which is then reacted with N-(2-amino-4,6-dichloropyrimidin-5-yl) formamide of the formula to give (1S,4R)- or (1R,4S)-4-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2-cyclopentenyl-1-methanol of the formulae and then cyclized to give the end compounds.

  本发明涉及一种新型的制备氨基醇的方法，该氨基醇的结构式为，可以是外消旋或内消旋，从2-氮杂双环[2.2.1]庚-5-烯-3-酮开始，进一步转化为相应的酰基衍生物，然后进一步转化为(1S,4R)-或(1R,4S)-4-(2-氨基-6-氯-9-H-嘌呤-9-基)-2-环戊烯基-1-甲醇，其结构式为。在后一种合成中，氨基醇转化为相应的D-或L-酒石酸盐，然后与N-(2-氨基-4,6-二氯嘧啶-5-基)甲酰胺反应，其结构式为，以给出(1S,4R)-或(1R,4S)-4-[(2-氨基-6-氯-5-甲酰基-4-嘧啶基)氨基]-2-环戊烯基-1-甲醇，其结构式为，然后环化以得到最终化合物。
• Process for the preparation of a racemic or optically active 4-(hydroxymethyl)-2-cyclopentene derivative
  申请人：Lonza A.G.

  公开号：US06262295B1

  公开（公告）日：2001-07-17

  A process for the preparation of a racemic or optically active compound of the formula where the group R1 is an unsubstituted or a halogen substituted C1-4-alkyl, a C1-4-alkoxy, an aryl, an arylalkyl, an aryloxy, or arylalkylloxy.

  一种制备式中R1为未取代或卤素取代的C1-4烷基、C1-4烷氧基、芳基、芳基烷基、芳基氧基或芳基烷氧基的外消旋或光学活性化合物的方法。
• Process for the preparation of (1S,4R)- or (1R,4S)-
  申请人：Lonza A.G.

  公开号：US06156893A1

  公开（公告）日：2000-12-05

  A novel process for the preparation of (1S,4R)- or (1R,4S)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclo-pentene-1-methanol of the formulae ##STR1## is described. This entails in the first stage (.+-.)-2-aza-bicyclo[2.2.1]hept-5-en-3-one of the formula ##STR2## being acylated to give a (.+-.)-2-azabicyclo[2.2.1]hept-5-en-3-one derivative of the general formula ##STR3## in which R.sup.1 denotes C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, aryl or aryloxy, the latter being reduced in the second stage to give a cyclopentene derivative of the general formula ##STR4## in which R.sup.1 has the stated meaning, the latter then being converted in the third stage biotechnologically into the (1R,4S)- or (1S,4R)-1-amino-4-(hydroxymethyl)-2-cyclopentene of the formula ##STR5## the latter being converted in the fourth stage with N-(2-amino-4,6-dichloro-5-pyrimidinyl)formamide of the formula ##STR6## into the (1S,4R)- or (1R,4S)-4-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2-cyclopente ne-1-methanol of the formulae ##STR7## and the latter being cyclized in the fifth stage in a known manner to the final product of the formula I or II.

  本发明描述了一种制备式为##STR1##的(1S,4R)-或(1R,4S)-4-(2-氨基-6-氯-9H-嘌呤-9-基)-2-环戊烯-1-甲醇的新工艺。其中，第一阶段涉及将式为##STR2##的(.+-.)-2-氮杂双环[2.2.1]庚-5-烯-3-酮酰化，得到一般式为##STR3##的(.+-.)-2-氮杂双环[2.2.1]庚-5-烯-3-酮衍生物，其中R.sup.1表示C.sub.1-4-烷基、C.sub.1-4-烷氧基、芳基或芳氧基，在第二阶段中，后者被还原为一般式为##STR4##的环戊烯衍生物，其中R.sup.1具有上述含义，然后在第三阶段中通过生物技术将后者转化为式为##STR5##的(1R,4S)-或(1S,4R)-1-氨基-4-(羟甲基)-2-环戊烯，最后在第五阶段中将后者环化为式为I或II的最终产物。第四阶段中，将式为##STR6##的N-(2-氨基-4,6-二氯-5-嘧啶基)甲酰胺与后者反应，得到式为##STR7##的(1S,4R)-或(1R,4S)-4-[(2-氨基-6-氯-5-甲酰胺-4-嘧啶基)氨基]-2-环戊烯-1-甲醇。
• Process for the preparation of aminoalcohol derivatives and their further conversion to (1R, 4S)-4(2-amino-6-chloro-5-formamido-4-pyrimidinyl)-amino-2-cyclopentenyl-1-methanol
  申请人：Lonza AG

  公开号：US07338945B2

  公开（公告）日：2008-03-04

  The invention relates to a novel process for the preparation of an aminoalcohol of the formula racemically or optically active, starting from 2-azabicyclo[2.2.1]hept-5-en-3-one, its further conversion to give the corresponding acyl derivative and its further conversion to (1S,4R)- or (1R,4S)-4-(2-amino-6-chloro-9-H-purine-9-yl)-2-cyclopentenyl-1-methanol of the formulae In the latter synthesis, the aminoalcohol is converted into the corresponding D- or L-tartrate, which is then reacted with N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide of the formula to give (1S,4R)- or (1R,4S)-4-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2-cyclopentenyl-1-methanol of the formulae and then cyclized to give the end compounds.

  本发明涉及一种从2-azabicyclo[2.2.1]庚-5-烯-3-酮出发制备racemically或光学活性的氨基醇的新工艺，以及其进一步转化为相应的酰基衍生物，再进一步转化为公式（1S,4R）-或（1R,4S）-4-（2-氨基-6-氯-9H-嘌呤-9-基）-2-环戊烯基-1-甲醇。在后者的合成中，氨基醇被转化为相应的D-或L-酒石酸盐，然后与公式中的N-（2-氨基-4,6-二氯嘧啶-5-基）甲酰胺反应，得到公式的（1S,4R）-或（1R,4S）-4-[(2-氨基-6-氯-5-甲酰胺-4-嘧啶基)氨基]-2-环戊烯基-1-甲醇，然后环化得到最终的化合物。